First enantioselective total synthesis of (-)-dysibetaine CPa and absolute configurations of natural product

被引：9

作者：

Sakai, Michihiro ^{[1
]}

Ishikawa, Yuichi ^{[1
]}

Takamizawa, Satoshi ^{[1
]}

Oikawa, Masato ^{[1
]}

机构：

[1] Yokohama City Univ, Kanazawa Ku, Yokohama, Kanagawa 2360027, Japan

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 44期

关键词：

Cyclopropane; Dysibetaine CPa; Enantioselective total synthesis; Quaternary ammonium group; Neuroactive natural product; Organocatalytic solvolysis; SPONGE DYSIDEA-HERBACEA; CINCHONA ALKALOIDS; AMINO-ACID; ANHYDRIDES; DYSIHERBAINE;

D O I：

10.1016/j.tetlet.2013.08.113

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here we report total synthesis of enantiomerically pure dysibetaine CPa, isolated from Micronesian marine sponge and expected to serve as a neuroactive agent. Starting from meso-cyclopropane triester, the synthesis was achieved in 12.8% overall yield over 10 steps including organocatalytic enantioselective solvolysis of meso-succinic anhydride as a key step. This work established the absolute configurations of the natural product as (3R,4R). (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5911 / 5912

页数：2

共 25 条

[1] Total synthesis of (±)-dysibetaine CPa
Oikawa, Masato
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TETRAHEDRON LETTERS, 2011, 52 (34) : 4402 - 4404
[2] Total Synthesis of (±)-Dysibetaine CPa and Analogs
Oikawa, Masato
Sasaki, Shota
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