title: Diastereoselective synthesis of the C17-C30 fragment of amphidinol 3.
abstract: The diastereoselective synthesis of the C17-C30 fragment of amphidinol 3 (AM3) 1 was achieved from the enantio-enriched aldehyde 20, Weinreb amide 14 and 2-bromo-3-(trimethylsilyl)propene, which was used as a bifunctional conjunctive reagent. The absolute configuration of the stereogenic centers, in both aldehyde 20 and Weinreb amide 14, were efficiently controlled by using (+)-(R)-methyl-p-tolylsulfoxide as the unique source of chirality.
authors.affiliation: CNRS/Université de Strasbourg (ECPM), UMR 7509, 25 Rue Becquerel, F-67087 Strasbourg, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Rival
authors.forename: Damien
authors.initials: D
authors.lastname: Hazelard
authors.forename: Gilles
authors.initials: G
authors.lastname: Hanquet
authors.forename: Thomas
authors.initials: T
authors.lastname: Kreuzer
authors.forename: Charlelie
authors.initials: C
authors.lastname: Bensoussan
authors.forename: Sébastien
authors.initials: S
authors.lastname: Reymond
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
authors.forename: Françoise
authors.initials: F
authors.lastname: Colobert
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry; D013237:Stereoisomerism; D000095722:Amphidinols
chemical_list: D000447:Aldehydes; D000475:Alkenes; D000577:Amides; D000814:Aniline Compounds; D011714:Pyrans; C554272:N-methyl-4-nitroaniline; C438973:amphidinol 3; D000095722:Amphidinols