A. Carpita, S. Braconi, R. Rossi*
Jul 18, 2005
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Influential Citations
9
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract The first total synthesis of naturally occurring (+)-gymnasterkoreayne F and its enantiomer is reported. The seven-step route to these two polyacetylenes in enantiomerically pure form involves the use of (+)-2,3- O -isopropylidene- l -threitol and (−)-2,3- O -isopropylidene- d -threitol, respectively, as the starting material and a Cadiot–Chodkiewicz reaction as a key step. The absolute configuration of (+)-gymnasterkoreayne F has been confirmed to be (2 E ,8 S , Z ). The natural product and its enantiomer have been found to exhibit modest cytotoxicity against the 60 human tumor cell lines of the National Cancer Institute.