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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Total synthesis of (+)-ambruticin S: probing the pharmacophoric subunit.

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.[1]

References

  1. Total synthesis of (+)-ambruticin S: probing the pharmacophoric subunit. Hanessian, S., Focken, T., Mi, X., Oza, R., Chen, B., Ritson, D., Beaudegnies, R. J. Org. Chem. (2010) [Pubmed]
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