Total Syntheses of Lycopodium Alkaloids (+)-Fawcettimine, (+)-Fawcettidine, and (−)-8-Deoxyserratinine

A shared story: Three fawcettimine‐ and serratinine‐type Lycopodium alkaloids are prepared from a common tetracyclic spirodiketone intermediate in concise total syntheses (see scheme). The intermediate was constructed by a remarkable biosynthesis‐inspired transannular NC bond formation to the spiro...

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Published inAngewandte Chemie (International ed.) Vol. 51; no. 2; pp. 491 - 495
Main Authors Li, Houhua, Wang, Xiaoming, Lei, Xiaoguang
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 09.01.2012
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
alkaloids
Alkaloids - chemical synthesis
Biological Products - chemical synthesis
Chemistry
Chemistry, Multidisciplinary
collective synthesis
Indolizines - chemical synthesis
Ketones - chemical synthesis
Ketones - chemistry
Lycopodium - chemistry
natural products
Physical Sciences
samarium iodide
Science & Technology
tandem reactions
(+)-COMPLANADINE
SERRATININE
alkaloids
CARBONYL-COMPOUNDS
samarium iodide
(+)-LYCOFLEXINE
collective synthesis
CLEAVAGE
HEXAMETHYLPHOSPHORIC TRIAMIDE HMPA
ALCOHOLS
natural products
REDUCTION
GLYCINOECLEPIN-A
HELQUIST ANNULATION
tandem reactions
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Summary:A shared story: Three fawcettimine‐ and serratinine‐type Lycopodium alkaloids are prepared from a common tetracyclic spirodiketone intermediate in concise total syntheses (see scheme). The intermediate was constructed by a remarkable biosynthesis‐inspired transannular NC bond formation to the spiro‐configured carbon center and a hydroxy‐directed pinacol coupling promoted by SmI2.
Bibliography:NSFC - No. 20802050; No. 21072150
National High Technology Projects 863 - No. 2008AA022317
Program for New Century Excellent Talents in University - No. NCET-10-0614
We thank Prof. David Zhigang Wang (Peking University Shenzhen Graduate School) and Dr. Shaohui Wang for helpful discussions, Mingyan Zhao and Rui Liu (NIBS) for NMR and HPLC-MS analysis, and Dr. Jiang Zhou (Peking University) for HRMS analysis. Financial support from the National High Technology Projects 863 (2008AA022317), the Program for New Century Excellent Talents in University (NCET-10-0614), and the NSFC (20802050, 21072150) is gratefully acknowledged.
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ArticleID:ANIE201106753
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We thank Prof. David Zhigang Wang (Peking University Shenzhen Graduate School) and Dr. Shaohui Wang for helpful discussions, Mingyan Zhao and Rui Liu (NIBS) for NMR and HPLC‐MS analysis, and Dr. Jiang Zhou (Peking University) for HRMS analysis. Financial support from the National High Technology Projects 863 (2008AA022317), the Program for New Century Excellent Talents in University (NCET‐10‐0614), and the NSFC (20802050, 21072150) is gratefully acknowledged.
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SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201106753