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Enantio- and diastereoselective synthesis of N-acetyl dihydrotetrafibricin methyl ester.

ABSTRACT: A highly diastereoselective synthesis of N-acetyl dihydrotetrafibricin methyl ester (34) is described. The synthesis features three enantioselective double allylboration reactions and an intramolecular hydrosilylation/Fleming-Tamao oxidation sequence to establish seven of the hydroxy-bearing stereocenters of 34. Especially noteworthy is the fragment-assembly double allyboration reaction of 2 and 7 using reagent 3, which provides the advanced intermediate 6 with >20:1 diastereoselectivity.

SUBMITTER: Nuhant P

PROVIDER: S-EPMC3679187 | biostudies-literature | 2013 Apr

REPOSITORIES: biostudies-literature

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Enantio- and diastereoselective synthesis of N-acetyl dihydrotetrafibricin methyl ester.

Nuhant Philippe P Roush William R WR

Journal of the American Chemical Society 20130326 14

A highly diastereoselective synthesis of N-acetyl dihydrotetrafibricin methyl ester (34) is described. The synthesis features three enantioselective double allylboration reactions and an intramolecular hydrosilylation/Fleming-Tamao oxidation sequence to establish seven of the hydroxy-bearing stereocenters of 34. Especially noteworthy is the fragment-assembly double allyboration reaction of 2 and 7 using reagent 3, which provides the advanced intermediate 6 with >20:1 diastereoselectivity. ...[more]

PMID: 23530855

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