title: Enantioselective synthesis of (10S)- and (10R)-methyl-anandamides.
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, and provides the analogs without the need for resolution. Peptide coupling, P-2 nickel partial hydrogenation, and cis-selective Wittig olefination are the key steps.
authors: Center for Drug Discovery, Northeastern University, 116 Mugar Life Sciences Building, 360 Huntington Avenue, Boston, MA 02115, USA.
authors: Spyros P
authors: SP
authors: Nikas
authors: Marsha
authors: M
authors: D'Souza
authors: Alexandros
authors: A
authors: Makriyannis
keywords: Enantioselective synthesis; Endocannabinoids; Lipids; Methyl-anandamide