Straightforward synthesis of panaxytriol: an active component of Red Ginseng.
A total synthesis of (3R,9R,10R)-panaxytriol (1) was accomplished enantioselectively (40% overall yield; 30% for the longest sequence). A key step was a Cadiot-Chodkiewicz cross-coupling reaction on two fragments containing, in the aggregate, three unprotected hydroxyl groups. One fragment was synthesized by a highly enantioselective reduction of an enynone. The other arose from a highly enantioselective dihydroxylation of an allylic alcohol.
Yun
Heedong
H
Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, New York 10027, USA. s-danishefsky@ski.mskcc.org
Danishefsky
Samuel J
SJ
D000480:Alkynes; D002384:Catalysis; D053281:Enediynes; D005233:Fatty Alcohols / Q000032:analysis / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D005894:Panax / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D053281:Enediynes; D005233:Fatty Alcohols; D007202:Indicators and Reagents; C057682:panaxytriol