Synthesis of the marine compound (2R,5Z,9Z)-2-methoxyhexacosa-5,9-dienoic acid via a lipase-catalyzed resolution and a novel O-alkylation protocol

被引：10

作者：

Kulkarni, BA ^{[1
]}

Sharma, A ^{[1
]}

Gamre, S ^{[1
]}

Chattopadhyay, S ^{[1
]}

机构：

[1] Bhabha Atom Res Ctr, Div Bioorgan, Bombay 400085, Maharashtra, India

来源：

SYNTHESIS-STUTTGART | 2004年 / 04期

关键词：

O-alkylation biocatalyst; enantioselective synthesis; demospongic acid;

D O I：

10.1055/s-2004-815963

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compound has been synthesized by a facile route starting from 4-pentyn-1-ol. The enantioselectivity was attained by a strategy involving a lipase-catalyzed acetylation of a solid-phase immobilized long chain a-hydroxy acid. Another important feature of the synthesis was the formulation of an efficient HgO-catalyzed O-methylation of the a-hydroxy acids which proceeded without any racemization. The alkylation protocol was also highly efficient for selective mono-methylation/benzylation of symmetrical diols.

引用

页码：595 / 599

页数：5

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