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Synfacts 2008(9): 0904-0904
DOI: 10.1055/s-2008-1077987
DOI: 10.1055/s-2008-1077987
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of (±)-Minfiensine
Contributor(s):Philip KocienskiL. Shen, M. Zhang, Y. Wu, Y. Qin*
West China School of Pharmacy and Sichuan University, Chengdu, P. R. of China
Efficient Assembly of an Indole Alkaloid Skeleton by Cyclopropanation: Concise Total Synthesis of (±)-Minfiensine
Angew. Chem. Int. Ed. 2008, 47: 3618-3621
West China School of Pharmacy and Sichuan University, Chengdu, P. R. of China
Efficient Assembly of an Indole Alkaloid Skeleton by Cyclopropanation: Concise Total Synthesis of (±)-Minfiensine
Angew. Chem. Int. Ed. 2008, 47: 3618-3621
Further Information
Publication History
Publication Date:
22 August 2008 (online)
Key words
minfiensine - cyclopropanation - palladium - α-vinylation
Significance
A highly efficient synthesis of (±)-minfiensine features a three-step, one-pot cascade reaction initiated by cyclopropanation of indole A to give the tetracycle D in 50% yield.
Comment
The fifth and final ring was installed by an intramolecular Pd-catalyzed α-vinylation of ketone F. For an earlier asymmetric synthesis of minfiensine based on a Heck/iminium ion cyclization see: L. E. Overman and co-workers J. Am. Chem. Soc. 2005, 127, 10186.