Tetrahedron

Enantioselective synthesis of (10S)-and (10R)-methyl-anandamides

SP Nikas, M D'Souza, A Makriyannis

Index: Nikas, Spyros P.; D'Souza, Marsha; Makriyannis, Alexandros Tetrahedron, 2012 , vol. 68, # 31 p. 6329 - 6337

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Citation Number: 7

Abstract

For the development of novel endocannabinoid templates with potential resistance to hydrolytic and oxidative metabolism, we are targeting the bis-allylic carbons of the arachidonoyl skeleton. Toward this end, we recently disclosed the synthesis and preliminary biological data for the (13S)-methyl-anandamide. We report now the total synthesis of the (10S)-and (10R)-methyl-counterparts. Our synthetic approach is stereospecific, efficient, ...