Synthesis

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

BA Kulkarni, A Sharma, S Gamre, S Chattopadhyay

Index: Kulkarni, Bheemashankar A.; Sharma, Anubha; Gamre, Sunita; Chattopadhyay, Subrata Synthesis, 2004 , # 4 p. 595 - 599

Full Text: HTML

Citation Number: 9

Abstract

Abstract 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 α-hydroxy acid. Another important feature of the synthesis was the formulation of an efficient HgO-catalyzed O-methylation of the α-hydroxy acids which proceeded without any racemization. The alkylation protocol was also highly ...