Total Synthesis and Establishment of the Stereochemistry of Spiniferin-1, a Rare Planar Chiral Marine Natural Product with a 1,6-Methano[10]annulene Skeleton

Wei-Sheng Tian; Kai Ding; Yun-Shan Sun; Ling Chen; Zhen Lei

doi:10.1055/s-0032-1318105

Synthesis, Table of Contents

Synthesis 2013; 45(4): 438-447
DOI: 10.1055/s-0032-1318105

feature article

Total Synthesis and Establishment of the Stereochemistry of Spiniferin-1, a Rare Planar Chiral Marine Natural Product with a 1,6-Methano[10]annulene Skeleton

Wei-Sheng Tian*

Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Fax: +86(21)64166128 Email: wstian@mail.sioc.ac.cn

,

Kai Ding

Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Fax: +86(21)64166128 Email: wstian@mail.sioc.ac.cn

,

Yun-Shan Sun

Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Fax: +86(21)64166128 Email: wstian@mail.sioc.ac.cn

,

Ling Chen

Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Fax: +86(21)64166128 Email: wstian@mail.sioc.ac.cn

,

Zhen Lei

Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Fax: +86(21)64166128 Email: wstian@mail.sioc.ac.cn

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Abstract

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Dedicated to Professors Weishan Zhou and Qingjiang Liao on their 90th birthdays

Abstract

Spiniferin-1, a rare planar chiral natural product with a 1,6-methano[10]annulene skeleton, has been synthesized via a novel polyfluoroalkanosulfonyl fluoride induced cascade carbocation rearrangement reaction. Natural spiniferin-1 was established as a racemic mixture by comparing its specific rotation with those of our synthesized S_p -(+)-spiniferin-1 and its R_p -(–)-enantiomer.

Key words

spiniferin-1 - planar chirality - total synthesis - rearrangement - annulenes

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References

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