title: Stereoselective synthesis of (-)-amphidinolide E.
abstract: The total synthesis of (-)-amphidinolide E was accomplished by following a synthetic scheme that incorporates the labile C2 stereocenter at a very late stage. The oxolane unit was prepared by beta-alkoxyacrylate radical cyclization. The enyne metathesis reaction was employed for the synthesis of the side chain. The Kocienski-Julia reaction was used for the union of the two major fragments, and the Kita macrolactonization protocol was used for macrolide synthesis.
authors.affiliation: Department of Chemistry, Seoul National University, Seoul 151-747, Korea.
authors.forename: Chan Hyuk
authors.initials: CH
authors.lastname: Kim
authors.forename: Hyo Jung
authors.initials: HJ
authors.lastname: An
authors.forename: Won Kyo
authors.initials: WK
authors.lastname: Shin
authors.forename: Wei
authors.initials: W
authors.lastname: Yu
authors.forename: Sang Kook
authors.initials: SK
authors.lastname: Woo
authors.forename: Soon Kyu
authors.initials: SK
authors.lastname: Jung
authors.forename: Eun
authors.initials: E
authors.lastname: Lee
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004951:Esterification; D005609:Free Radicals / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D000097442:Amphidinolides
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D005609:Free Radicals; C452448:amphidinolide E; D000097442:Amphidinolides