title: Expedient synthesis of a stereoisomer of acremolide B.
abstract: A highly straightforward strategy for the synthesis of the acremolide class of lipodepsipeptides has been developed. Synthetic highlights include a cross-metathesis to couple the C1-C7 and the C8-C12 fragments, an esterification to introduce the dipeptide unit, a macrolactamization to build the macrolide core, and two stereoselective allylations/crotylations to control all four stereogenic centers of the C1-C12 polypropionate segment.
authors.affiliation: Laboratoire de Chimie Organique, ESPCI ParisTech, UMR CNRS 7084, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Abdelatif
authors.initials: A
authors.lastname: ElMarrouni
authors.forename: Aya
authors.initials: A
authors.lastname: Fukuda
authors.forename: Montserrat
authors.initials: M
authors.lastname: Heras
authors.forename: Stellios
authors.initials: S
authors.lastname: Arseniyadis
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
mesh_terms: D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D004951:Esterification; D055666:Lipopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D018942:Macrolides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009842:Oligopeptides / Q000737:chemistry*; D011422:Propionates / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D047630:Depsipeptides; D055666:Lipopeptides; D018942:Macrolides; D009842:Oligopeptides; D011422:Propionates; C556252:acremolides