title: Tandem enyne metathesis-metallotropic [1,3]-shift for a concise total syntheses of (+)-asperpentyn, (-)-harveynone, and (-)-tricholomenyn A.
abstract: A tandem reaction sequence involving relay metathesis-induced enyne RCM and metallotropic [1,3]-shift is an effective tool to construct cyclic alkenes with embedded 1,5-dien-3-yne moieties from acyclic precursors containing a 1,3-diyne. Total syntheses of (+)-asperpentyn, (-)-harveynone, and (-)-tricholomenyn A have been accomplished by implementing this metathesis-based tandem reaction sequence as the key step.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA.
authors.forename: Jingwei
authors.initials: J
authors.lastname: Li
authors.forename: Sangho
authors.initials: S
authors.lastname: Park
authors.forename: Reagan L
authors.initials: RL
authors.lastname: Miller
authors.forename: Daesung
authors.initials: D
authors.lastname: Lee
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D053138:Cyclohexenes / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D001688:Biological Products; D053138:Cyclohexenes; D004852:Epoxy Compounds; C538695:asperpentyn; C538696:harveynone; C538697:tricholomenyn A