title: Synthesis of the C-1-C-17 fragment of amphidinolides C, C2, C3, and F.
abstract: The C-1-C-17 fragment of amphidinolides C, C2, C3, and F has been constructed from a trans-2,5-disubstituted dihydrofuranone prepared by diastereoselective rearrangement of a free or metal-bound oxonium ylide generated from a metal carbenoid. The dihydrofuranone was converted into an aldehyde corresponding to the C-1-C-8 framework, and this was coupled to the C-9-C-17 unit by nucleophilic addition of a vinylic anion.
authors.affiliation: WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow, University Avenue, Glasgow G12 8QQ, United Kingdom. stephen.clark@glasgow.ac.uk
authors.forename: J Stephen
authors.initials: JS
authors.lastname: Clark
authors.forename: Guang
authors.initials: G
authors.lastname: Yang
authors.forename: Andrew P
authors.initials: AP
authors.lastname: Osnowski
mesh_terms: D004141:Dinoflagellida / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D000097442:Amphidinolides
chemical_list: D018942:Macrolides; C429132:amphidinolide C; D000097442:Amphidinolides