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DOI: 10.1055/s-0028-1087292
Synthesis of (±)-Lyconadin A
Contributor(s):Philip Kocienski, Stewart EcclesUniversity of California, Berkeley, USA
Unified Strategy for the Synthesis of the ”Miscellaneous" Lycopodium Alkaloids: Total Synthesis of (±)-Lyconadin A
J. Am. Chem. Soc. 2008, 130: 7222-7223
Publication History
Publication Date:
20 November 2008 (online)
Key words
(±)-lyconadin A - oxidative C-N bond formation - Saegusa-Ito oxidation
Significance
()-Lyconadin A is an unusual member of the Lycopodium alkaloid family, members of which possess varied biological activities. Reported here is a method to produce miscellaneous Lycopodium alkaloids from a common intermediate, forming the tetracyclic core by an oxidative C-N bond forming reaction.
Comment
A number of transformations were investigated for the key C-N bond formation. Treatment of H with n-BuLi (3 equiv) gave the dianion I, which reacted with I2 to give J in 80% yield. Similarly, exposure of the dianion I to NIS gave the C6- iodinated product, which could be converted into J by t-BuOK.