Novel approach for the introduction of a C-1 oxygenated group on the decalin skeleton: first asymmetric total synthesis of 1S,6S-dihydroxy-eudesm-3-ene.
This paper describes a novel approach for the introduction of a C-1 hydroxyl on the decalin ring system, starting from (-)-carvone. Utilizing the substrate-controlled Mukaiyama aldol reaction and alkaline cyclization as key steps, the C-1 oxygenated decalin eudesmane skeleton 2' and its four isomers were synthesized efficiently. Furthermore, X-ray structural analysis showed that the claimed structure for the natural product is incorrect.
Zheng
Guojun
G
State Key Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry Lanzhou University, Lanzhou, P. R. China.
Chen
Jinchun
J
Fang
Lijing
L
Guan
Yukun
Y
Li
Yulin
Y
D001685:Biological Factors / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D000081005:Cyclohexane Monoterpenes; D007536:Isomerism; D008958:Models, Molecular; D015394:Molecular Structure; D039821:Monoterpenes; D009281:Naphthalenes / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D045787:Sesquiterpenes, Eudesmane / Q000138:chemical synthesis* / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry
C492681:1,6-dihydroxyeudesm-3-ene; D001685:Biological Factors; D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D009281:Naphthalenes; D012717:Sesquiterpenes; D045787:Sesquiterpenes, Eudesmane; D013729:Terpenes; C006923:carvone; C007229:decalin