title: Biomimetic total synthesis of (+)-gelsemine.
abstract: Challenging: (+)-gelsemine was synthesized from (R,R)-aziridine 1 in 25 steps with approximately 1 % overall yield. A multistep, one-pot enol-oxonium cyclization cascade was used to construct, simultaneously, the E ring, F ring, C3 stereocenter, and C7 quaternary stereocenter. This synthesis using the enol-oxonium cyclization reaction as a key step to make the cage structure has demonstrated the proposed biosynthetic pathway of the gelsemine family.
authors.affiliation: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, Sichuan University, Chengdu, China.
authors.forename: Xuan
authors.initials: X
authors.lastname: Zhou
authors.forename: Tao
authors.initials: T
authors.lastname: Xiao
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Iwama
authors.forename: Yong
authors.initials: Y
authors.lastname: Qin
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry; D032701:Biomimetics / Q000379:methods; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; C063230:gelsemine