Stereoelectronic and steric control in chiral cyclohexane synthesis toward (-)-tetrodotoxin

被引：24

作者：

Bamba, M ^{[1
]}

Nishikawa, T ^{[1
]}

Isobe, M ^{[1
]}

机构：

[1] Nagoya Univ, Sch Bioagr Sci, Organ Chem Lab, Nagoya, Aichi 4648601, Japan

来源：

TETRAHEDRON | 1998年 / 54卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(98)00331-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of important intermediates for tetrodotoxin has been explored. The chiral cyclohexane ring was constructed by electrocyclization from a triene precursor and by conversion to the highly oxygenated cyclohexane ring. In particular, the introduction of an a-hydroxy group at the 5 position (toxin-numbering) in tetrodotoxin was achieved by allylic oxidation with SeO(2). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6639 / 6650

页数：12

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