title: Donor-acceptor substituted cyclopropane to butanolide and butenolide natural products: enantiospecific first total synthesis of (+)-hydroxyancepsenolide.
abstract: An oxygen substituted donor-acceptor cyclopropane (DAC) is used as a common intermediate in the enantiospecific collective total synthesis of butanolide- and butenolide-based natural products like (+)-juruenolide C and D, (+)-blastmycinone, (+)-antimycinone, and (+)-ancepsenolide. Enantiospecific first total syntheses of (+)-hydroxyancepsenolide and its acetate are achieved confirming their absolute stereochemistry.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay , Powai, Mumbai 400076, India.
authors.forename: Santosh J
authors.initials: SJ
authors.lastname: Gharpure
authors.forename: Laxmi Narayan
authors.initials: LN
authors.lastname: Nanda
authors.forename: Manoj Kumar
authors.initials: MK
authors.lastname: Shukla
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000968:Antimycin A / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D004149:Dioxoles / Q000138:chemical synthesis* / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D003521:Cyclopropanes; D004149:Dioxoles; D007783:Lactones; C416059:blastomycinone; C000600289:hydroxyancepsenolide; C437388:juruenolide C; C032456:antimycin; D000968:Antimycin A; C004511:butenolide; C030797:cyclopropane; D015107:4-Butyrolactone