Enantioselective total synthesis of valeriananoids A-C.
[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.
Srikrishna
A
A
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India. ask@orgchem.iisc.ernet.in
Satyanarayana
G
G
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
D000081005:Cyclohexane Monoterpenes; D007202:Indicators and Reagents; D039821:Monoterpenes; D012717:Sesquiterpenes; D013729:Terpenes; C495640:valeriananoid A; C495641:valeriananoid B; C495642:valeriananoid C; C006923:carvone