Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 11, Pages 4519-4522Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0341665
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Funding
- NHLBI NIH HHS [HL25848] Funding Source: Medline
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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.
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