title: Synthesis of (-)-swainsonine and (-)-8-epi-swainsonine by the addition of allenylmetals to chiral α,β-alkoxy sulfinylimines.
abstract: The asymmetric synthesis of (-)-swainsonine and (-)-8-epi-swainsonine is reported through the addition of either the allenylzinc or the allenyl lithio cyanocuprate reagents derived from [3-(methoxymethoxy)prop-1-ynyl]trimethylsilane to enantiopure α,β-dialkoxy N-tert-butanesulfinylimines derived from d-erythronolactone.
authors.affiliation: UPMC-Univ Paris 6, UMR CNRS 7201, Institut Parisien de Chimie Moléculaire, Institut de Chimie Moléculaire (FR 2769), case 183, 4 Place Jussieu, 75005 Paris, France.
authors.forename: Julien
authors.initials: J
authors.lastname: Louvel
authors.forename: Fabrice
authors.initials: F
authors.lastname: Chemla
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Demont
authors.forename: Franck
authors.initials: F
authors.lastname: Ferreira
authors.forename: Alejandro
authors.initials: A
authors.lastname: Pérez-Luna
mesh_terms: D000438:Alcohols / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry; D017026:Swainsonine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C569913:8-epi-swainsonine; D000438:Alcohols; D007097:Imines; D013441:Sulfinic Acids; C059688:alkoxyl radical; D017026:Swainsonine