Synthesis of 4,5-seco-eudesman-type sesquiterpenes: 4,5-dioxo-10-epi-4,5-seco-gamma-eudesmane and 4,5-dioxo-10-epi-4,5-seco-gamma-eudesmanol.
A facile synthetic route to two seco-eudesmanes, 4,5-dioxo-10-epi-4,5-seco-gamma-eudesmane (1) and 4,5-dioxo-10-epi-4,5-seco-gamma-eudesmol (2) from (+)-dihydrocarvone has been described. Avoiding expensive reagents, this highly economic method is especially suited for the synthesis of 4,5-seco-eudesman-type and iphionan-type sesquiterpenes with a double bond at positions 11 and 12.
Fang
Lijing
L
State Key Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou University, Lanzhou, P. R. China.
Chen
Jinchun
J
Zheng
Guojun
G
Zhang
Chen
C
Li
Yulin
Y
D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D045787:Sesquiterpenes, Eudesmane / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D012717:Sesquiterpenes; D045787:Sesquiterpenes, Eudesmane; C006923:carvone