Synthesis of the C42-C52 part of ciguatoxin CTX3C

被引：42

作者：

Domon, D ^{[1
]}

Fujiwara, K ^{[1
]}

Ohtaniuchi, Y ^{[1
]}

Takezawa, A ^{[1
]}

Takeda, S ^{[1
]}

Kawasaki, H ^{[1
]}

Murai, A ^{[1
]}

Kawai, H ^{[1
]}

Suzuki, T ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 48期

关键词：

ciguatoxin CTX3C; natural product synthesis; reductive ring-opening; oxidative cyclization;

D O I：

10.1016/j.tetlet.2005.09.163

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C42-C52 part of ciguatoxin CTX3C (1) was synthesized from tri-O-acetyl D-glucal. The synthetic segment had a tetrahydropyran ring corresponding to the 'C49-reduced' L-ring of 1, designed to avoid side reactions due to acid-labile C49 acetal carbon during acidic reductive conditions planned in further synthesis toward 1. The vicinal dimethyl part at C47-C48 was constructed by a stepwise conjugate addition/methylation procedure. The C50-C52 unit was installed by Grignard addition of the C-3 unit followed by of the spirocyclic acetal. Stereoselective assembly of the C42-C44 part was achieved by Brown's asymmetric crotylboration. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：8279 / 8283

页数：5

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