title: Total syntheses of amphidinolides T1, T3, and T4.
abstract: Concise and high-yielding total syntheses of amphidinolides T1, T3, and T4 have been completed using an alkynyl macrolactone as a common late-stage intermediate. The required α-hydroxy ketone motif was installed by sequential alkyne hydrosilylation, epoxidation, and Fleming-Tamao oxidation. An oxonium ylide rearrangement formed the trisubstituted tetrahydrofuran core found in the natural products.
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (UK) http://www.chem.gla.ac.uk/staff/stephenc/. stephen.clark@glasgow.ac.uk.
authors.forename: J Stephen
authors.initials: JS
authors.lastname: Clark
authors.forename: Filippo
authors.initials: F
authors.lastname: Romiti
mesh_terms: D001688:Biological Products; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D000097442:Amphidinolides
chemical_list: D001688:Biological Products; D018942:Macrolides; C540231:amphidinolide T1; D000097442:Amphidinolides
keywords: diazo ketone; natural products; oxidation; rearrangement; total synthesis