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Synfacts 2017; 13(10): 1013
DOI: 10.1055/s-0036-1591235
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Biomimetic Total Synthesis of (±)-Naphthomevalin

Contributor(s):
Erick M. Carreira
,
Robert J. Gillespie
Miles ZD. Diethelm S. Pepper HP. Huang DM. George JH. * Moore BS. * University of Adelaide, Australia and Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, La Jolla, USA
A Unifying Paradigm for Naphthoquinone-Based Meroterpenoid (Bio)Synthesis.

Nat. Chem. 2017;
DOI: 10.1038/nchem.2829
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Further Information

Publication History

Publication Date:
18 September 2017 (online)

 
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Key words

(±)-naphthomevalin - meroterpenoid biosynthesis - oxidative dearomatization - α-ketol rearrangement - biomimetic synthesis

Significance

The total synthesis of (±)-naphtho­mevalin, a biologically active meroterpenoid was accomplished. The synthesis is exemplified by the incorporation of several biomimetic steps. Additionally, the authors report two enzymatically catalyzed reactions which are analogous to those used in the chemical synthesis, implying their importance in meroterpenoid biosynthesis.


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Comment

Compound B was generanylated and then subjected to a bio-inspired, one-pot oxidative dearomatization–chlorination to afford E in 53% yield. After introduction of a prenyl group and MOM deprotection, the key biomimetic α-ketol rearrangement was utilized to afford the natural product in quantitative yield.


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