A cross-metathesis approach to novel pantothenamide derivatives

Beilstein Journal of Organic Chemistry

Lekha Puri¹  Matthew Hachey¹  Karine Auclair¹  Jinming Guan¹  Kevin J. Saliba²  Vanessa Howieson² 

[1] Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, H3A 0B8, Canada;Research School of Biology, College of Medicine, Biology and Environment, The Australian National University, Canberra, Australian Capital Territory, 2601, Australia;

关键词: antibiotic;    antiplasmodial;    coenzyme A;    metathesis;    pantothenate;   

DOI  :  10.3762/bjoc.12.95

来源: DOAJ

【 摘 要 】

Pantothenamides are known for their in vitro antimicrobial activity. Our group has previously reported a new stereoselective route to access derivatives modified at the geminal dimethyl moiety. This route however fails in the addition of large substituents. Here we report a new synthetic route that exploits the known allyl derivative, allowing for the installation of larger groups via cross-metathesis. The method was applied in the synthesis of a new pantothenamide with improved stability in human blood.

【 授权许可】

Unknown