title: Synthesis of key fragments of amphidinolide Q--a cytotoxic 12-membered macrolide.
abstract: β-hydroxy aldehyde and alkyl ketone moieties were effectively synthesized as key intermediates of amphidinolide Q, a cytotoxic macrolide from the cultured dinoflagellate Amphidinium sp.. The asymmetric center of the former derivative was produced by Sharpless asymmetric epoxidation, followed by E-selective 1,4-addition to give the sp² methyl group. Derivatization of the L-ascorbic acid derivative by Evans asymmetric alkylation and Peterson olefination provided the latter intermediate. The coupling reaction of the segments was examined.
authors.affiliation: Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Kohei
authors.initials: K
authors.lastname: Kawa
authors.forename: Akihiro
authors.initials: A
authors.lastname: Hara
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Ishikawa
authors.forename: Shigeru
authors.initials: S
authors.lastname: Nishiyama
mesh_terms: D001205:Ascorbic Acid; D004141:Dinoflagellida / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D000097442:Amphidinolides
chemical_list: D001205:Ascorbic Acid; D018942:Macrolides; C532855:amphidinolide Q; D000097442:Amphidinolides