title: Total synthesis of (+)-mupirocin H from D-glucose.
abstract: Enantioselective total synthesis of mupirocin H is accomplished starting from D-glucose featuring strategic application of D-glucose derived chirality, diastereoselective Still-Barrish hydroboration, and further elaboration of carbon chain to furnish a phenyltetrazolyl sulfone intermediate, which on coupling with (2S,3S)-2-methyl-3-(triisopropylsilyloxy)butanal under Julia-Kocienski olefination conditions gave an advanced E-olefinic intermediate selectively. The E-olefin was transformed to the 4-hydroxynitrile, a prefinal substrate, which on acid-catalyzed oxidative lactonization furnished the target molecule mupirocin H in 19 steps from known compound 6 (longest linear sequence) with an overall yield of 4.96%.
authors.affiliation: CSIR-Indian Institute of Chemical Technology, Hyderabad 500607, India.
authors.forename: Sandip P
authors.initials: SP
authors.lastname: Udawant
authors.forename: Tushar Kanti
authors.initials: TK
authors.lastname: Chakraborty
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D005947:Glucose / Q000737:chemistry*; D015394:Molecular Structure; D016712:Mupirocin / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D016712:Mupirocin; D005947:Glucose