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Determination of the absolute configuration of marine oxylipin topsentolide A1 by the synthesis of the enantiomer of the natural product

✍ Scribed by Munetaka Kobayashi; Ken Ishigami; Hidenori Watanabe

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 553 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.03.071

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✦ Synopsis

Topsentolide A 1 Nine-membered lactone Determination of the absolute configuration Marine oxylipin a b s t r a c t Two possible stereoisomers of topsentolide A 1 , a cytotoxic oxylipin against human solid tumor cell lines, were prepared in order to determine the stereochemistry of natural product. That is, the enantiomer of topsentolide A 1 , (8S,11S,12R)-isomer, and its diastereomer was efficiently synthesized in a stereoselective manner. The stereochemistry of topsentolide A 1 was determined to be 8R,11R,12S by comparing NMR spectra and specific rotations of the synthetic isomers and the natural product.

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