title: Studies toward the total synthesis of sorangiolides and their analogues. A convergent stereoselective synthesis of the macrocyclic lactone precursors.
abstract: Stereoselective synthesis of the fully protected 18-membered macrocyclic lactones as the immediate precursors of the natural products, sorangiolides A and B, is described. The key steps used in the synthesis include the sp3-hybridized carbon-carbon Fu cross coupling, the stereoselective Evans' aldol reaction with 1,5-anti induction, the 1,3-diastereoselective syn reduction of a beta-hydroxyketone intermediate, and Mukaiyama macrolactonization reactions.
authors.affiliation: The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Sanjib
authors.initials: S
authors.lastname: Das
authors.forename: Sunny
authors.initials: S
authors.lastname: Abraham
authors.forename: Subhash C
authors.initials: SC
authors.lastname: Sinha
mesh_terms: D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D007850:Lauric Acids / Q000138:chemical synthesis / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D007850:Lauric Acids; D047028:Macrocyclic Compounds; C096605:sorangiolid A; C521909:sorangiolide B