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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.

SUBMITTER: Nikas SP

PROVIDER: S-EPMC3849710 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature

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

Nikas Spyros P SP D'Souza Marsha M Makriyannis Alexandros A

Tetrahedron 20120801 31

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 ...[more]

PMID: 24319298

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