Diastereo- and enantioselective synthesis of allylsilane. A useful C-ring fragment of taxol.

被引：11

作者：

Kusama, H ^{[1
]}

Mori, T ^{[1
]}

Mitani, I ^{[1
]}

Kashima, H ^{[1
]}

Kuwajima, I ^{[1
]}

机构：

[1] TOKYO INST TECHNOL,DEPT CHEM,TOKYO 152,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(97)00843-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective synthesis of a taxol C-ring fragment containing an allylsilane moiety is described. Diastereoselective \4 + 2\ cycloaddition of the pyrone with (R)-t-butylbenzyl vinyl ether followed by appropriate transformations gave a mixture of two regioisomeric cyclohexenyl sulfides, which was convened to the title compound with almost complete diastereo- and enantioselectivities by treating with Li and 4,4'-di-t-butylbiphenyl followed by quenching with chlorotrimethylsilane. (C) 1997 Elsevier Science Ltd.

引用

页码：4129 / 4132

页数：4

共 38 条

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[6] A concise synthetic approach to optically active taxol C-ring fragment
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[7] Synthesis of the C-ring fragment of cobyric acid
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[9] Ring Opening/C-N Cyclization of Activated Aziridines with Carbon Nucleophiles: Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines
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[10] Asymmetric synthesis of a taxol C-ring by aldol condensation and radical cyclization
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