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Concise total syntheses of the Lycopodium alkaloids (+/-)-nankakurines A and B via luciduline.

ABSTRACT: Total syntheses of the Lycopodium alkaloids nankakurines A and B have been accomplished in 6 and 7 steps, respectively, via a sequence that passes through a third Lycopodium alkaloid, luciduline, and forgoes the use of protecting groups on nitrogen. Key features include a short preparation of luciduline followed by a concise and stereoselective aminoallylation/ring-closing metathesis protocol to fashion the spiropiperidine ring common to nankakurines A and B.

SUBMITTER: Cheng X

PROVIDER: S-EPMC2804776 | biostudies-literature | 2010 Jan

REPOSITORIES: biostudies-literature

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Concise total syntheses of the Lycopodium alkaloids (+/-)-nankakurines A and B via luciduline.

Cheng Xiayun X Waters Stephen P SP

Organic letters 20100101 2

Total syntheses of the Lycopodium alkaloids nankakurines A and B have been accomplished in 6 and 7 steps, respectively, via a sequence that passes through a third Lycopodium alkaloid, luciduline, and forgoes the use of protecting groups on nitrogen. Key features include a short preparation of luciduline followed by a concise and stereoselective aminoallylation/ring-closing metathesis protocol to fashion the spiropiperidine ring common to nankakurines A and B. ...[more]

PMID: 20014779

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