BARC/PUB/2004/0554

 
 

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

 
     
 
Author(s)

Kulkarni, B. A.; Sharma, A.; Gamre, S.; Chattopadhyay, S.
(BOD)

Source

Synthesis, 2004. (4): pp. 595-599

ABSTRACT

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

 
 
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