Combinatorial synthesis of the 1,5-polyol system based on cross metathesis: structure revision of amphidinol 3.
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.
Oishi
Tohru
T
Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka, Japan. oishi@chem.sci.osaka-u.ac.jp
Kanemoto
Mitsunori
M
Swasono
Respati
R
Matsumori
Nobuaki
N
Murata
Michio
M
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
D000475:Alkenes; D011108:Polymers; D011714:Pyrans; C438973:amphidinol 3; D000095722:Amphidinols; C024617:polyol