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 13C NMR data of the synthetic specimens with that of AM3 led to a controversy regarding the orig...

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Bibliographic Details
Published in:Organic letters 2008-11, Vol.10 (22), p.5203-5206
Main Authors: Oishi, Tohru, Kanemoto, Mitsunori, Swasono, Respati, Matsumori, Nobuaki, Murata, Michio
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Combinatorial Chemistry Techniques
Magnetic Resonance Spectroscopy
Polymers - chemical synthesis
Polymers - chemistry
Pyrans - chemistry
Stereoisomerism
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Summary: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 13C 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol802168r