title: A cross-metathesis approach to novel pantothenamide derivatives.
abstract: 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.
authors.affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, H3A 0B8, Canada.
authors.forename: Jinming
authors.initials: J
authors.lastname: Guan
authors.affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, H3A 0B8, Canada.
authors.forename: Matthew
authors.initials: M
authors.lastname: Hachey
authors.affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, H3A 0B8, Canada.
authors.forename: Lekha
authors.initials: L
authors.lastname: Puri
authors.affiliation: Research School of Biology, College of Medicine, Biology and Environment, The Australian National University, Canberra, Australian Capital Territory, 2601, Australia.
authors.forename: Vanessa
authors.initials: V
authors.lastname: Howieson
authors.affiliation: Research School of Biology, College of Medicine, Biology and Environment, The Australian National University, Canberra, Australian Capital Territory, 2601, Australia; Medical School, College of Medicine, Biology and Environment, The Australian National University, Canberra, Australian Capital Territory, 2601, Australia.
authors.forename: Kevin J
authors.initials: KJ
authors.lastname: Saliba
authors.affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, H3A 0B8, Canada.
authors.forename: Karine
authors.initials: K
authors.lastname: Auclair
keywords: antibiotic; antiplasmodial; coenzyme A; metathesis; pantothenate