Synthesis of a highly hindered hydrindanone via alpha-carbonyl radical cyclization: enantiospecific formal syntheses of (-)-pinguisenol and (-)-alpha-pinguisene.
An enantiospecific synthesis of Schinzer's ketone 3 from (R)-(+)-pulegone via alpha-carbonyl radical cyclization was accomplished. This work also constitutes an enantiospecific formal syntheses of (-)-pinguisenol and (-)-alpha-pinguisene. The intermediate ketone 4 would be useful for the synthesis of other pinguisane-type sesquiterpenes.
Sha
Chin-Kang
CK
Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan, ROC. cksha@mx.nthu.edu.tw
Liao
Hau-Wei
HW
Cheng
Ping-Chang
PC
Yen
Shih-Chieh
SC
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D003500:Cyclization; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D007659:Ketones; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C482624:alpha-pinguisene; C482623:pinguisenol