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.
State Key Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry Lanzhou University, Lanzhou, P. R. China.
Guojun
G
Zheng
Jinchun
J
Chen
Lijing
L
Fang
Yukun
Y
Guan
Yulin
Y
Li
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