Concise synthesis of the chemopreventitive agent (+/-)-deguelin via a key 6-endo hydroarylation.
[reaction: see text]. A concise total synthesis of (+/-)-deguelin was achieved with a longest linear sequence of six steps in 68% yield. A key step was the platinum-catalyzed 6-endo hydroarylation of an alkynone intermediate.
Department of Chemistry, Columbia University, New York, New York 10027, USA.
Stefan J
SJ
Pastine
Dalibor
D
Sames
D001952:Bridged-Ring Compounds / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D017671:Platinum Compounds / Q000737:chemistry; D012402:Rotenone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D001952:Bridged-Ring Compounds; D017671:Platinum Compounds; D012402:Rotenone; C030173:platinum chloride; C107676:deguelin