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. 2010 Jan 15;12(2):205-7.
doi: 10.1021/ol902455y.

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

Xiayun Cheng  1 , Stephen P Waters
Affiliations

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

Xiayun Cheng et al. Org Lett. .

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.

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Figures

Figure 1
Figure 1
The Lycopodium alkaloids nankakurines A and B and their structural relationship to luciduline.
Scheme 1
Scheme 1
Selected Bond Formations toward the Nankakurines
Scheme 2
Scheme 2
A Three-Step Total Synthesis of Luciduline
Scheme 3
Scheme 3
Syntheses of Nankakurines A and B
See this image and copyright information in PMC

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