title: Bioinspired total synthesis of bolivianine: a Diels-Alder/intramolecular hetero-Diels-Alder cascade approach.
abstract: We report the first total synthesis of bolivanine in a 14-step pathway involving the synthesis of onoseriolide. Our synthesis features a palladium-catalyzed intramolecular cyclopropanation involving an allylic metal carbene and a Diels-Alder/intramolecular hetero-Diels-Alder cascade, allowing the single-step assembly of a tricyclic system with proper configuration. The synthetic efforts validate our modified biogenetic hypothesis and allow us to confirm the absolute configuration of bolivianine.
authors.affiliation: Key Laboratory of Green Chemistry & Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China.
authors.forename: Changchun
authors.initials: C
authors.lastname: Yuan
authors.forename: Biao
authors.initials: B
authors.lastname: Du
authors.forename: Li
authors.initials: L
authors.lastname: Yang
authors.forename: Bo
authors.initials: B
authors.lastname: Liu
mesh_terms: D008968:Molecular Conformation; D012717:Sesquiterpenes / Q000737:chemistry; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D012717:Sesquiterpenes; D013729:Terpenes; C524834:bolivianine; C551646:onoseriolide