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DOI: 10.1055/a-2013-9885
Recent Advances in the Dearomative Skeletal Editing of Mono-azaarenes
This work was supported by the National Natural Science Foundation of China (22101073 and U1504206), the Key Teacher Project of Henan Province of China (2021GGJS025), China Postdoctoral Science Foundation (2020M672200), and Henan University (SYL20060149).
Abstract
Despite its challenges, the skeletal editing of mono-azaarenes (pyridines, quinolines, and isoquinolines) has shown unparalleled synthetic utility in the construction of complex molecules that are difficult to access by conventional methods. In this short review, we summarize the three most recently developed skeletal editing strategies for the deconstruction of azaarene cores, with a focus on their generality, limitations, and mechanistic aspects. Also, the application of the skeletal editing strategy in the total synthesis of some important natural products is discussed.
1 Introduction
2 Skeletal Editing of Mono-Azaarenes through Zincke-like Reactions
3 Skeletal Editing of Mono-azaarenes through Aza-Buchner Reactions
4 Skeletal Editing of Mono-azaarenes via Photoinduced Radical or Energy-Transfer Processes
5 Conclusion
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Key words
mono-azaarene - dearomatization - skeletal editing - functionalization - Zincke reaction - Buchner reaction - photoinduced reactionIntroduction
Nitrogen-containing heterocycles are widely encountered in natural products and pharmaceuticals.[1] Of the top 200 selling U.S. FDA-approved organic small molecule drugs in 2014, 59% contain at least one aza-heterocycle, and most of them are saturated or partially saturated six-membered azaheterocycles.[2] Mono-azaarenes, including pyridines, quinolines, and isoquinolines, are readily available feedstock chemicals that constitute the core skeletons of many bioactive natural products and pharmaceuticals.[2] In addition, thanks to their ready availability and fruitful reactive properties, they are also important synthetic precursors in the construction of complex functionalized molecules and they have useful applications in material science and synthetic catalysis. Therefore, exploitation of versatile azaarene-based chemical transformations to construct high-value-added products is of great significance. Among the well-established synthetic tactics, dearomative functionalization of azaarenes has flourished; it has the capacity to convert planar azaarenes into three-dimensional azaheterocycles with complete or partial saturation.[3] Although considerable progress has been made, this strategy only modifies the periphery of the aza-heteroaromatic rings through C–H functionalization, while the six-membered aza-heterocyclic core is retained. Complementary to this, skeletal editing could rapidly and conveniently accomplish the core framework alteration by breaking the innate molecular skeleton to produce reactive intermediates followed by reconstruction to generate complex and diverse molecules. However, in sharp contrast with the overwhelming dearomative functionalization of azaarenes, the development of dearomative skeletal editing is still in its infancy. This is possibly caused by the following issues: (1) high resonance stabilization energy needs to be overcome to break their aromaticity, and (2) dissociating the stable six-membered aza-heterocyclic structure is a thermodynamically unfavorable process. Despite the great challenges, this research area has aroused extensive interest among the chemical community and some significant advances have been achieved.
In this short review, we wish to present a timely summarization of the latest research advances and breakthroughs in the skeletal editing of mono-azaarenes and its application in the total synthesis of natural products. In addition, the generality and limitations of each method and the in-depth mechanism are also discussed. Based on the three commonly used approaches to break the mono-azaarene rings, this review is organized into three sections: (i) skeletal editing of mono-azaarenes through Zincke-like reactions, (ii) skeletal editing of mono-azaarenes through aza-Buchner reactions, and (iii) skeletal editing of mono-azaarenes via photoinduced radical or energy-transfer processes (Scheme [1]). We hope this review will inspire readers to explore more fascinating and robust approaches to advance the development of the skeletal editing of mono-azaarenes, thus enabling this strategy to become an efficient synthetic tool to access more complex and useful molecules that are difficult to access.
# 2
Skeletal Editing of Mono-azaarenes through Zincke-like Reactions
The study of dearomative ring-opening reactions of mono-azaarenes began in the early 20th century. In 1903, Zincke reported that N-aryl-activated pyridinium salts (Zincke salts) underwent amine exchange on reaction with primary amines, but the reaction with secondary amines generated ring-opened 5-aminopenta-2,4-dienals (Scheme [2]).[4] This method is termed the ‘Zincke reaction’. In 1904, König used N-CN activated pyridinium salts (König salts) with the same experimental outcomes.[5] The mechanism of these reactions involves attack of the amine at the C2-position of the pyridinium to generate in situ an unstable N,N-ketal resulting in the ring-opening of the pyridine core. After these precedents, the skeletal editing of azaarenes received considerable attention and remarkable progress was made in the fields of organic synthesis,[6] material chemistry,[7] and catalysis.[8] Herein, we wish to summarize their recent advances in synthetic methodologies.
Using the Instability of N,O-Ketals as the Driving Force
The Trofimov group have made a considerable contribution to the field of skeletal remodeling of mono-azaarenes (Scheme [3]).[9] They accomplished the ring-opening of pyridines 3-1 by reaction with alkynones 3-2 to give stable 5-[(Z)-2-(acylvinyl)amino]penta-2,4-dienals 3-3 in 84–92% yields (Scheme [3a]).[9a] [b] Mechanistically, this reaction begins with the in situ activation of pyridines 3-1 by reaction with alkynones 3-2, followed by ring-opening via the formation of unstable N,O-ketal intermediates to give the final 5-[(Z)-2-(acylvinyl)amino]penta-2,4-dienals 3-3. Despite its highly efficient, this strategy suffers from regio- and stereoselectivity issues. Replacing pyridines with quinolines and isoquinolines gave the desired ring-opened products 3-6 and 3-7, but they were unstable and easily underwent oligomerization. By using slightly modified conditions, a novel reconstruction of quinolines 3-4 took place that conveniently gave 2-aryl-3-acylquinolines 3-8 in up to 66% yield.[9c] [d] As shown in Scheme [3b], this reaction proceeded by a cascade process involving the cleavage of the pyridine ring, insertion of the alkynone, and elimination of one molecule of acetaldehyde.
In 2020, the Fu group reported an I2-mediated ring-contraction reaction of pyridinium iodides 4-1, which provided an easy access to 2-formylpyrroles 4-2 in 18–86% yields (Scheme [4]).[10] In this transformation, both K2CO3 and I2 were indispensable and they work together to make this reaction occur successfully. The base K2CO3 promoted the generation of unstable N,O-aminals, in which the C–N bond was prone to undergo cleavage. The I2 behaved as an electrophilic cation to transform the alkene into a three-membered iodonium ring. The reaction was also successful for an N-methylisoquinolinium salt and gave isoindole 4-2c albeit in 29% yield. However, unsubstituted pyridinium salts, an N-methylquinolinium salt, and a 1-methyl-1,10-phenanthrolinium salt failed to participate in this reaction.
The Lankalapalli group disclosed the skeletal editing of 1,2-dihydropyridines (DHPs) 5-1 to give 2-pyridones 5-3 (Scheme [5]).[11] In the key step, 1,2-dihydropyridines 5-1 were smoothly oxidized with DDQ to give pyridiniums 5-2 that were treated with potassium carbonate to give 5-3. Mechanistically, pyridinium 5-2 is easily intercepted by water to produce N,O-ketal intermediate 5-A; this is unstable and the ring is cleaved leading to intermediate 5-B bearing an amino group and an ester group. Then, intramolecular lactamization of 5-B takes place to afford 2-pyridone 5-3.
In 2021, the Wu group unlocked a new reactivity of 8-aminoquinolines 6-2 by reaction with aryl methyl ketones 6-1 in the presence of I2 and FeCl3, in which the ring-opening of 8-aminoquinolines was accomplished to produce a set of imidazole-based acrylaldehydes 6-3 in 51–85% yields (Scheme [6]).[12] Mechanistically, this reaction is initiated by the iodination/Kornblum oxidation sequence of acetophenone (6-1a), with the assistance of I2, to produce phenylglyoxal 6-B. Then, an imine 6-D is produced from the condensation of phenylglyoxal 6-B and 8-aminoquinoline 6-2. In the presence of HI and FeCl3, the imine 6-D is activated (6-E) and easily undergoes intramolecular cyclization to form iminium ion 6-F, which is immediately intercepted by water to deliver N,O-hemiacetal intermediate 6-G. Taking advantage of the instability of the N,O-hemiacetal in 6-G opens the quinoline ring to give 6-H and this is aromatized to give 6-3a.
# 2.2
Using the Instability of N,N-Ketals as the Driving Force
In 2019, Morofuji, Kano, and Kinoshita reported a [5+1] cycloaddition of Zincke’s salts 7-1 and aryl methyl ketones (Scheme [7]),[13] in which the deconstructive ring-opening of 7-1 was realized with the assistance of piperidine to generate donor-π-acceptor (D-π-A) streptocyanine intermediates 7-2. Then, streptocyanines 7-2 served as 5C sources to participate in the [5+1] cycloaddition with aryl methyl ketones through a nucleophilic addition, deamination, E/Z-isomerization, electrocyclization, and aromatization sequence, thus producing a new benzene ring. This transformation offered an efficient and rapid approach to carbonyl-p-phenylene-π molecules, some of which possessed the structural characters of C 3-symmetric donor-acceptors.
The Klán group developed an efficient approach to substituted heptamethine cyanines through the ring-opening of Zincke salts 8-1 (Scheme [8]).[14] In this transformation, 4-bromoaniline played the dual role of facilitating pyridinium ring opening and activating the resulting imine for facile condensation with quaternized heterocycles. The substituents on the pyridine rings were incorporated into the cyanines as a part of the heptamethine scaffold to enrich their structural diversity.
In 2020, the Zhang group accomplished the dearomative deconstruction of N-alkyl-activated quinoliniums salts 9-1 by a cascade strategy merging hydrogen transfer and selective coupling, which offered a reliable approach to functionalized arylamines 9-3 in 38–85% yields (Scheme [9]).[15] In this process, 2-aminoarylmethanols 9-2 function as hydrogen donors to reduce the quinoliniums 9-1 to dihydroquinolines 9-4 and are themselves oxidized to ortho-aminobenzaldehydes 9-5. The latter (9-5) possess a nucleophilic amine group and electrophilic carbonyl group, which confers on them the capacity to intercept the thus generated 9-4 to undergo intermolecular annulation producing the polycyclic intermediates 9-7. Subsequently C–N bond cleavage is driven by the inherent N,N-aminal instability affording products 9-3. These mild reaction conditions exhibited a broad functional group tolerance, including cyano and alkenyl groups, which are susceptible to react under reducing conditions. In addition, substrates containing biological scaffolds were also compatible.
Subsequently, the Zhang group expanded the hydride-transfer-initiated reaction system to isoquinolinium salts 10-1 (Scheme [10]).[16] Unfortunately, the reaction conditions (Ru catalyst base) used for quinoliniums 9-1 failed to give the desired product when using isoquinolinium salts 10-1 with 2-aminoarylmethanols 9-2. However, replacing 2-aminoarylmethanols 9-2 with 2-aminobenzaldehydes 10-2 in the reaction with isoquinolinium salts 10-1 and using PhSiH3 as an external hydride source successfully promote the reaction to produced functionalized quinolines 10-3 in up to 92% yields. Differing from their previous report, the hydride transfer process proceeded under metal-free conditions.
In 2021, Morofuji, Kano, and Inagawa reported an efficient method to prepare a series of meta-substituted anilines 11-3 from pyridines 11-1 (Scheme [11]).[17] In this work, the aryl group activated pyridines underwent a sequential ring-opening and ring-closing reaction, with the nitrogen atom in pyridine ring replaced by a methane group and a dialkylamino substituent introduced. This cascade reaction tolerated a wide range of 4-substituted pyridines and secondary amines. Biologically useful amines, such as maprotiline and fluoxetine, were successfully incorporated, thus leading to 11-2e and 11-2f in 75% and 81% yields, respectively.
The examples discussed so far use external amines as nucleophiles to generate unstable N,N-ketals and to induce the subsequent ring-opening. As an important complement, the Vanderwal group designed new pyridine synthons by incorporating a nucleophilic aniline at the C3 position of the pyridine core in 12-1 that on treatment with cyanogen bromide followed by aqueous ammonium chloride gave 3-indol-3-ylpropenals 12-2 in 63–80% yields (Scheme [12a]).[18a] As expected, 12-1 undergoes in situ König activation as their pyridinium salt 12-A, and then the internal amine serves as a nucleophilic site to attack the pyridinium ring easily to give 12-B, which undergoes deconstructive ring-opening of pyridinium core to give 3-indol-3-ylpropenal 12-2. A similar process occurred for 3-[2-(benzoylamino)ethyl]pyridine (12-3), but additional dimethylamine was required to ensure productive reactivity. After workup under basic conditions, the desired N-benzoyl-4,5-dihydropyrrole 12-5 was obtained in 57% overall yield. They utilized this ring-opening strategy in a concise formal synthesis of porothramycins A and B (Scheme [12b]).[18b]
# 2.3
The Reactivities of Aminopentadienal Intermediates
The aminopentadienals generated from the ring-opening of pyridinium cores possess versatile reactivities that can undergo fruitful chemical transformations. For instance, after activation by POCl3, the aminopentadienal 13-2 was transformed into chloropentadiene iminium intermediate 13-3, which was highly reactive and was intercepted by various active methylene compounds to generate hexa-1,3,5-trienes 13-4 (Scheme [13]).[19] In addition, upon activation of aminopentadienal 13-2 with acetyl chloride, the thus generated intermediate 13-5 was used as a diene to participate in [4+2] cycloaddition with one or two molecules of N-phenylmaleimide to produce 13-6 in 18% and 13-7 in 24% yields, respectively. To further enrich the reactivity of 13-2, an endocyclic enamine, masked as its aminonitrile precursor 13-8, was employed as reaction partner and gave, surprisingly, aminopentadiene iminium salt 13-9, accompanied by a trace amount of 13-10. A mechanistic analysis revealed that two equivalents of aminopentadienal 13-2 were involved in this transformation, with the destruction of the inherent cyclic structure of 13-8.
In 2008, the Vanderwal group demonstrated that the aminopentadienals 14-2 were easily converted into δ-tributylstannyl-α,β,γ,δ-unsaturated aldehydes (stannyldienals) 14-3 by reaction with tributylstannyllithium (Scheme [14]).[20] In this reaction, tributylstannyllithium served as a nucleophile to regioselectively undergo 1,6-conjugate addition with aminopentadienals 14-2 with the unusual loss of dimethylamide anion as a leaving group, thus enabling the synthesis of 14-3 in 35–67% yields. The stannyldienals 14-3 were valuable synthons, which participated in Stille couplings with iodoalkene 14-4 and iodobenzene (14-6) to give polyenes 14-5 and 14-7, respectively, bearing a transformable aldehyde functional group with the conservation of alkene geometries.
Due to their structural ‘push-pull’ electron nature caused by the electron-donating amine and the electron-withdrawing terminal aldehyde, aminopentadienals are capable of behaving as dienes to participate in normal or inverse-electron-demand [4+2] cycloadditions. For instance, the Vanderwal group utilized tryptamine derivatives 15-1 as N sources attacking the Zincke salts 15-2 to promote the ring-opening of the pyridinium core, thus enabling the synthesis of aminopentadienals 15-3 bearing an internal indole ring (Scheme [15]).[21] In the presence of base, the intramolecular inverse-electron-demand [4+2] cycloaddition between indole and aminopentadienal proceeded smoothly to deliver the key architecture of many indoline-based natural products. By tuning the R substituents and performing various post-modifications, natural products, such as strychnine, norfluorocurarine, akuammicine, and alsmaphorazine B, were synthesized. This elegant work not only demonstrates the synthetic charm of this skeletal editing strategy, but also enriches the application of tryptamine chemistry in the synthesis of bioactive molecules.[22]
The Vanderwal group also designed a new Zincke aldehyde 16-1 tethered to an alkyne functional group and anticipated that it would undergo intramolecular Diels–Alder reaction. An unexpected rearrangement occurred upon heating Zincke aldehyde 16-1 at 160 °C for 16 h to give the synthetically useful α,β,γ,δ-unsaturated amides 16-2 with the prospective dienophile remaining intact (Scheme [16a]).[23a] This reaction tolerated a broad range of Zincke aldehydes and had an excellent Z-selectivity (Scheme [16b]). Interestingly, when N-allyl- or N-homoallyl-substituted Zincke aldehydes 16-4 were used, an additional Diels–Alder cycloaddition occurred, thus enabling access to polycyclic lactams 16-6 in 30–82% yields (Scheme [16c]).[23b] Computational studies revealed that a thermally instigated E to Z isomerization proceeds first to generate 16-A (Scheme [16d]).[23c] Afterward, an intramolecular 1,5-sigmatropic shift of hydrogen takes place to afford transient vinylketene intermediate 16-B; cyclization and 6π electrocyclic ring-opening sequence gives α,β,γ,δ-unsaturated amide 16-5. The cyclic nature of the intermediate 16-C accounts for the Z geometry of the product. If the amine is N-allyl-substituted then intramolecular Diels–Alder cycloaddition occurs.
The cases discussed above show that the in situ generated N,N-ketals have the capacity to deconstruct the azaarene ring, thereby generating a reactive aminopentadienal intermediate. However, these reactions suffer from atom-economy issues because the activated groups are released as waste in the form of primary amines. To overcome this issue, the Wang group designed a new chalcone-containing pyridinium salts based on their previous studies on the dearomatization of activated azaarenes.[24] In these chalcone-containing pyridinium salts, the chalcone moiety not only plays the crucial role in activating the pyridinium core, but also participates as an efficient reactive group in a subsequent cascade process (Scheme [17]).[25] The Wang group have achieved an unprecedented intramolecular [4+2] cycloaddition between 5-aminopenta-2,4-dienals, generated in situ from pyridine deconstruction, and the chalcone moiety to give structurally complex isoindoline polycycles. In these transformations, two kinds of driving forces were used to break the pyridinium core: one was the commonly used instability of N,N-ketals, and the other was the newly unveiled instability of cyclic β-amino ketones when using 1,3-dicarbonyl compounds as nucleophiles.
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# 3
Skeletal Editing of Mono-azaarenes through Aza-Buchner Reactions
Activated azaarenes also undergo aza-Buchner reaction to achieve the ring-expansion of azaarenes, thus leading to the formation of cyclic conjugated aza-trienes. In 2004, the Yadav group reported the first copper-catalyzed ring-expansion of N-acylated quinolines 18-1 and isoquinolines 18-4 to give benzoazepines 18-3 and 18-5, respectively, in excellent yields with a high degree of selectivity (Scheme [18a]).[26a] In 2021, the Beeler group developed a simple method for the dearomative ring-expansion of azaarene-based N-ylides 18-6, 18-8, and 18-10 (Scheme [18b]).[26b] This reaction proceeded through a photochemically dependent ylide rearrangement. Excited by visible light, a singlet diradical is generated via an n to π* transition. Then, the excited species undergoes radical recombination to form an aza-norcaradiene intermediate. Finally, 6π-electrocyclic ring opening affords azepine products. When R1 is H, further rearrangement takes place via 1,5-H shift or proton transfer.
# 4
Skeletal Editing of Mono-azaarenes via Photoinduced Radical or Energy-Transfer Process
Due to the electron-poor characteristic, pyridiniums can also be used as electron acceptors to participate in one-electron process. In 2021, the Tang and Pan group disclosed a visible-light-driven skeletal remodeling strategy of pyridinium salts that smoothly converted 19-1 into 3-formylpyrroles 19-2 with easily available rhodamine B as the photosensitizer (Scheme [19]).[27] The key to the success is the formation of unstable 1,2-dioxetane intermediate 19-D, which is the driving force for subsequent cleavage of the pyridine ring to dicarbaldehyde intermediate 19-F. Once 19-F is generated, the intramolecular aldol reaction occurs with the assistance of base to produce the desired 19-2. Interestingly, the replacement of rhodamine B with cobalt tetramethoxyphenylporphyrin as the photosensitizer resulted in the controllable synthesis of 4-carbonylpyridines 19-3 from pyridinium salts 19-1 without any substituents on the pyridine ring.
Indoles are not only privileged structural units of many bioactive molecules, but also important chemical feedstocks to assemble biologically interesting compounds.[28] Therefore, it is of great significance to develop efficient approaches to access indoles. In 2022, the Levin group reported an elegant ring contraction of quinoline N-oxides 20-1 to produce N-acylindoles 20-3 by extruding a carbon atom from the quinoline core through a sequential process comprising of selective photolysis and acid-promoted arrangement (Scheme [20]).[29] This strategy has potential to be amenable to a wide range of medicinally relevant functional groups, regardless of their electronic properties and substitution positions. Moreover, this reaction was accomplished in a one-pot fashion, with the in situ formation of the N-oxide from commercially available 2-methylquinoline (20-4) by oxidation with H2O2 followed by relay visible-light- and acid-induced scaffold hopping. Notably, this one-pot procedure gave only slightly reduced yield of 20-3a compared with the two-pot process (69% vs 78%). Mechanistically, this strategy begins with the intramolecular annulation of quinoline N-oxides 20-1 under irradiation of visible light (390 nm) to afford oxaziridine 20-5, which is in equilibrium with intermediate 20-6 and ring-enlarged 3,1-benzoxazepine 20-2. Then, benzoxazepine 20-2 undergoes hydrolysis under the action of acid through two concurrent pathways to produce 20-9. Finally, an intramolecular condensation delivers the desired N-acylindole 20-3. This work exhibited the great capacity for direct scaffold hopping from quinoline N-oxides to indole through a C2-selective carbon deletion.
For fused azaarenes, such as quinolines, it is not the prerogative of the azocyclic ring to undergo skeletal recombination; the benzenoid moiety can also undergo dearomative skeleton editing. In 2022, the Glorius group unveiled the multi-faceted reactivities of the benzenoid core in quinolines through a photoinduced cascade energy transfer process, which smoothly accomplished the scaffold hopping of the benzenoid cores (Scheme [21]).[30] These reactions provided a straightforward approach to pyridine-fused 6-5-4-3- and 6-4-6-membered ring systems through two distinct pathways by simply tuning the substituents on the benzene ring. The reactions between 6-chloroquinolines 21-1 and haloalkenes 21-2 afforded the structurally unique pyridine-fused 6-5-4-3 ring system 21-3 with broad functionality compatibility. This transformation is proposed to be initiated by an energy-transfer-mediated [2+2] cycloaddition to produce intermediate 21-I. A subsequent C–Cl bond homolytic cleavage through a second energy-transfer process furnishes a triplet radical pair (from 21-II to 21-III), followed by C–C and C–Cl bond formation to give the terminal products 21-3. Notably, the 7-chloroquinoline was also amenable to this reaction and produced 21-3h in 87% yield as the sole diastereomer. However, the reaction between quinoline-8-carboxylate 21-4 and vinyl acetates 21-5 proceeded via a different pathway to produce the polycyclic pyridines 21-6 fused with a 6-4-6-membered ring system. Differing from the mechanism for the formation of 21-3, a ring expansion occurs, through a second energy-transfer process, to yield a biradical (from 21-V to 21-VI), followed by intramolecular radical-radical coupling to give product 21-6. This work not only provided a robust and convenient method to access pyridine-fused polycycles, which are hardly accessible, but also represented an uncommon dearomative skeleton recombination of benzenoid rings.
# 5
Conclusions
Although the dearomative skeletal editing of azaarenes is challenging, impressive progress has been made since the seminal reports by Zincke in 1903. A series of approaches have been tactically established and their synthetic capacity has been exploited as the key step in the total synthesis of various biologically active natural products and functionalized molecules. However, there are still some important issues to be addressed, including: (1) The current strategies have atom-economy issues. To destroy the azaarenes, stoichiometric amines are required and they together with the N-activating group of the generated amines are released when the reaction goes to completion. Thus, the exploration of a more efficient catalytic system is in high demand. (2) The driving force for the deconstruction of azaarenes needs to be further developed. At this stage, the driving forces are limited to the formation of unstable N,O- or N,N-ketals, β-amino ketones, strained small rings, or thermodynamically unstable seven-membered rings. Accordingly, tailored substrates are required to meet the requirement of ring-opening, thus resulting in limited substrate scope. (3) These reactions often suffer from regioselectivity issues. This was especially the case when primary or secondary amines serving as nucleophiles attack unsymmetrically substituted pyridiniums. Both the C2- and the C6-positions of pyridiniums are electrophilic and the amines can not efficiently distinguish the subtle reactivity difference of these reaction sites, thus resulting in regioselectivity issues. (4) There has been no asymmetric variant reported. We believe that with the continuous efforts of chemists, these challenges will be skillfully resolved and this research area will flourish. We hope that the skeletal editing strategy will become a preferable synthetic tool to assemble complex natural products, drugs, and organic materials in the future.
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Conflict of Interest
The authors declare no conflict of interest.
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Corresponding Authors
Publication History
Received: 19 December 2022
Accepted after revision: 16 January 2023
Accepted Manuscript online:
17 January 2023
Article published online:
16 February 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
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