Synthesis of the C8-C20 and C21-C30 segments of pectenotoxin 2

被引：18

作者：

Fujiwara, Kenshu ^{[1
]}

Aki, Yu-ichi ^{[1
]}

Yamamoto, Fuyuki ^{[1
]}

Kawamura, Mariko ^{[1
]}

Kobayashi, Masanori ^{[1
]}

Okano, Azusa ^{[1
]}

Awakura, Daisuke ^{[1
]}

Shiga, Shunsuke ^{[1
]}

Murai, Akio ^{[1
]}

Kawai, Hidetoshi ^{[1
]}

Suzuki, Takanori ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 26期

关键词：

pectenotoxin; 2; natural product synthesis; polyether macrolide;

D O I：

10.1016/j.tetlet.2007.04.136

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study, we synthesized the C8-C20 and C21-C30 segments of the diarrhetic shellfish toxin pectenotoxin 2. The C8C20 segment was assembled from a phosphonate corresponding to the C8-C15 segment (prepared from L-malic acid in 19 steps) and an aldehyde corresponding to the C16-C20 segment (synthesized from 3-methyl-3-butenol in nine steps) by a twelve-step process including the Homer-Wadsworth-Emmons reaction, regio- and stereoselective reduction of the resulting enone, diastereoselective epoxidation, and 5-exo epoxide cleavage forming the C-ring. The C21-C30 segment was constructed in 13 steps from (S)-glycidol via a route involving E-ring formation by 5-exo epoxide cleavage and stereoselective methylation at C27 by the Evans method. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：4523 / 4527

页数：5

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