title: Total synthesis and revision of the absolute configuration of seimatopolide B.
abstract: The asymmetric total synthesis of natural seimatopolide B along with its enantiomer is described starting from readily available 5-hexen-1-ol and 3-buten-1-ol. The key steps involved are Jacobson hydrolytic kinetic resolution, proline-catalyzed α-hydroxylation, Yamaguchi esterification and ring-closing metathesis. This asymmetric total synthesis necessitates the revision of the originally assigned (3R, 6S, 9S)-configuration to (3S, 6R, 9R).
authors.affiliation: Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, India. rajireddy@iict.res.in
authors.forename: Chada Raji
authors.initials: CR
authors.lastname: Reddy
authors.forename: Uredi
authors.initials: U
authors.lastname: Dilipkumar
authors.forename: Motatipally Damoder
authors.initials: MD
authors.lastname: Reddy
authors.forename: Nagavaram Narsimha
authors.initials: NN
authors.lastname: Rao
mesh_terms: D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; C573611:seimatopolide B