title: Enantioselective total synthesis of valeriananoids A-C.
abstract: [reaction: see text] The first enantioselective total synthesis of valeriananoids A-C (-)-1-3 is reported starting from the readily available monoterpene (R)-carvone, employing a tandem intermolecular Michael addition-intramolecular Michael addition-alkylation sequence and an electron-transfer-mediated 6-endo-trig cyclization as key steps.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India. ask@orgchem.iisc.ernet.in
authors.forename: A
authors.initials: A
authors.lastname: Srikrishna
authors.forename: G
authors.initials: G
authors.lastname: Satyanarayana
mesh_terms: D000478:Alkylation; D002384:Catalysis; D003500:Cyclization; D000081005:Cyclohexane Monoterpenes; D007202:Indicators and Reagents; D015394:Molecular Structure; D039821:Monoterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry*; D014632:Valerian / Q000737:chemistry
chemical_list: D000081005:Cyclohexane Monoterpenes; D007202:Indicators and Reagents; D039821:Monoterpenes; D012717:Sesquiterpenes; D013729:Terpenes; C495640:valeriananoid A; C495641:valeriananoid B; C495642:valeriananoid C; C006923:carvone