Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 16, Pages 5601-5618Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo100956v
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Funding
- Syngenta (Basel, Switzerland)
- NSERC
- FQRNT
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An enantioselective synthesis of the antifungal natural product (+)-ambruticin S has been accomplished starting with the readily available methyl alpha-D-glucopyranoside, (R)-Roche ester, and (S)-glycidol as chirons, which encompassed seven of the 10 stereogenic centers of the target molecule. The remaining three centers were set by a highly diastereoselective, asymmetric cyclopropanation employing a chiral, nonracemic phosphonamide reagent. Our strategy for the construction of the dihydropyran subunit involved a highly syn-selective Lewis acid catalyzed 6-endo-trig cyclization. Other key steps in the synthesis featured an epoxide opening with a dithiane anion, two efficient phosphonamide-anion based olefinations, and a late-stage C-glycosylation.
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