title: Combinatorial synthesis of the 1,5-polyol system based on cross metathesis: structure revision of amphidinol 3.
abstract: Combinatorial synthesis of a 1,5-polyol system corresponding to the C1-C14 unit of amphidinol 3 (AM3) and its diastereomers was achieved via chemoselective cross metathesis as the key step. Comparison of (13)C NMR data of the synthetic specimens with that of AM3 led to a controversy regarding the originally proposed structure. From GC-MS analysis of the degradation product, the absolute configuration at C2 of AM3 has been revised to be R.
authors.affiliation: Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka, Japan. oishi@chem.sci.osaka-u.ac.jp
authors.forename: Tohru
authors.initials: T
authors.lastname: Oishi
authors.forename: Mitsunori
authors.initials: M
authors.lastname: Kanemoto
authors.forename: Respati
authors.initials: R
authors.lastname: Swasono
authors.forename: Nobuaki
authors.initials: N
authors.lastname: Matsumori
authors.forename: Michio
authors.initials: M
authors.lastname: Murata
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D009682:Magnetic Resonance Spectroscopy; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry*; D013237:Stereoisomerism; D000095722:Amphidinols
chemical_list: D000475:Alkenes; D011108:Polymers; D011714:Pyrans; C438973:amphidinol 3; D000095722:Amphidinols; C024617:polyol