title: Stereoselective synthesis of the C1-C11 and C12-C34 fragments of mycalolide A.
abstract: A convergent synthesis of the C1-C11 and C12-C34 fragments of mycalolide A is described. Synthetic highlights include a highly E-selective cross-metathesis between a vinyl-functionalized bis-oxazole unit and a polypropionate side chain to introduce the C19-C20 double bond and an enzymatic desymmetrization of a meso-diol in addition to five stereoselective allylations/crotylations to control the 11 stereogenic centers present in the natural product.
authors.affiliation: Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Hoffman
authors.forename: Amandine
authors.initials: A
authors.lastname: Kolleth
authors.forename: James H
authors.initials: JH
authors.lastname: Rigby
authors.forename: Stellios
authors.initials: S
authors.lastname: Arseniyadis
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
mesh_terms: D000818:Animals; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008387:Marine Toxins; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; D008387:Marine Toxins; D010080:Oxazoles; C553072:mycalolide A