Stereoselective syntheses of four diastereomers of 3,9,12-trihydroxycalamenene via a benzobicyclo[3.3.1] intermediate.
The highly stereoselective syntheses of four diastereomers of natural 3,9,12-trihydroxycalamenene are described. The syntheses highlight the utility of an unusual framework of benzobicyclo[3.3.1] lactones, which were accomplished via an intramolecular Friedel-Crafts-type Michael addition of alpha,beta-unsaturated lactones.
Sun
Yongquan
Y
State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou, 730000, People's Republic of China.
Yu
Binxun
B
Wang
Xiaolei
X
Tang
Shibing
S
She
Xuegong
X
Pan
Xinfu
X
D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D000081223:Polycyclic Sesquiterpenes; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D001643:Bridged Bicyclo Compounds; D007783:Lactones; D000081223:Polycyclic Sesquiterpenes; D013729:Terpenes; C502644:calamenene