title: Stereodivergent Synthesis and Configurational Assignment of the C1-C15 Segment of Amphirionin-5.
abstract: The relative configuration of the C3-C12 portion of amphirionin-5, a novel marine polyketide with potent cell proliferation-promoting activity, was established by the stereodivergent synthesis of six diastereomeric model compounds and comparison of their NMR spectroscopic data with those reported for the natural product. This study led to the elucidation of the relative configuration between C4/C5 and C9/C12 and to the reassignment of the proposed configuration of the C9 position of amphirionin-5.
authors: Moemi
authors: M
authors: Kanto
authors: Department of Chemistry, Graduate School of Science, Tohoku University , 6-3 Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-8578, Japan.
authors: Sota
authors: S
authors: Sato
authors: Faculty of Agriculture and Marine Science and Center for Advanced Marine Core Research, Kochi University , Kochi 783-8502, Japan.
authors: Masashi
authors: M
authors: Tsuda
authors: Makoto
authors: M
authors: Sasaki
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D049109:Cell Proliferation / Q000187:drug effects; D008386:Marine Biology; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D066244:Proton Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D061065:Polyketides; C000607861:amphirionin-5