Studies directed toward asymmetric synthesis of cardioactive steroids via anionic polycyclization.
[reaction: see text] The use of anionic polycyclization (AP) in constructing the steroidal backbone of cardenolides was investigated. The reaction of 2-carbomethoxy-2-cyclohexenone I with the enolate of Nazarov reagent II gave, after decarboxylation and aldol condensation, steroid III with control of stereochemistry.
Yang
Zhixiang
Z
Laboratoire de synthèse organique, Institut de pharmacologie de Sherbrooke, Université de Sherbrooke, Sherbrooke, Québec J1H 5N4, Canada.
Shannon
Dean
D
Truong
Vouy-Linh
VL
Deslongchamps
Pierre
P
D002298:Cardenolides / Q000138:chemical synthesis; D002316:Cardiotonic Agents / Q000138:chemical synthesis*; D003500:Cyclization; D010042:Ouabain / Q000138:chemical synthesis; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis*
D002298:Cardenolides; D002316:Cardiotonic Agents; D013256:Steroids; D010042:Ouabain