title: 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.
authors.affiliation: Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, USA.
authors.forename: Philippe
authors.initials: P
authors.lastname: Nuhant
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
mesh_terms: D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: D018942:Macrolides; C583626:N-acetyl dihydrotetrafibricin methyl ester; C082780:tetrafibricin