Toward the total synthesis of tetrodotoxin: stereoselective construction of the 7-oxanorbornane intermediate

被引：10

作者：

Manabe, Atsushi ^{[1
]}

Ohfune, Yasufumi ^{[1
]}

Shinada, Tetsuro ^{[1
]}

机构：

[1] Osaka City Univ, Grad Sch Sci, Sumiyoshi Ku, Osaka 5588585, Japan

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 44期

关键词：

Tetrodotoxin; Diels-Alder reaction; Nitroolefin; Furan; EFFICIENT TOTAL-SYNTHESIS; OPTICALLY-ACTIVE TETRODOTOXIN; ASYMMETRIC TOTAL-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; DIELS-ALDER; CHEMICAL-SYNTHESIS; UNNATURAL ANALOG; D-GLUCOSE; 8,11-DIDEOXYTETRODOTOXIN; DERIVATIVES;

D O I：

10.1016/j.tetlet.2014.09.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective synthesis of 7-oxanorbornane regarding as a key synthetic intermediate of tetrodotoxin (TTX) is reported. The bicyclo ring bearing various functional groups was successfully elaborated by a furan Diels-Alder (DA) reaction. The stereoselective installation of a quaternary amino carbon center to the DA product was achieved with the Tsuji-Trost allylation. The stereochemistry was unambiguously confirmed with X-ray. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：6077 / 6080

页数：4

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