title: Multicomponent Strategy for the Synthesis of Prostaglandin E2 Methyl Ester under Anion Relay Chelation Control.
abstract: Starting with four components, the enantioselective synthesis of prostaglandin E2 methyl ester has been achieved through a highly stereoselective heteroatom-directed conjugate addition reaction and cyclopentanone ring cyclization as the key steps. This asymmetric strategy includes (i) an asymmetric Reformatsky reaction; (ii) conjugate addition of a chiral vinyllithium reagent; (iii) cyclization to form a sulfonylated cyclopentanone in one-pot; followed by (iv) allylation of the side chain. Four carbon-carbon bond-forming processes and three stereogenic centers were established, with the steps from (ii) to (iii) being achieved in a one-pot process.
authors.affiliation: Department of Chemistry, National Tsing Hua University , Hsinchu, 30013, Taiwan (ROC).
authors.forename: Kuan-Hsun
authors.initials: KH
authors.lastname: Huang
authors.affiliation: Department of Chemistry, National Tsing Hua University , Hsinchu, 30013, Taiwan (ROC).
authors.forename: Chun-Chieh
authors.initials: CC
authors.lastname: Huang
authors.affiliation: Department of Chemistry, National Tsing Hua University , Hsinchu, 30013, Taiwan (ROC).
authors.forename: Minoru
authors.initials: M
authors.lastname: Isobe