The first total synthesis of naturally occurring (−)-nitidon and its enantiomer is reported. The best of the routes investigated for preparation of these enantiomerically pure compounds involves a modification of the Cadiot−Chodkiewicz reaction and the Sharpless asymmetric epoxidation of an (E)-2-ene-4,6-diyn-1-ol as key steps and proceeds in five steps and 18% overall yield. Both enantiomers of nitidon and some related 6-(1,3-diyn-1-yl)-2H-pyran-2-ones have been found to exhibit significant cytotoxic activity against human cancer cell lines in vitro.

First total synthesis of naturally-occurring (–)-nitidon and its enantiomer

BELLINA, FABIO;CARPITA, ADRIANO;ROSSI, RENZO
2004

Abstract

The first total synthesis of naturally occurring (−)-nitidon and its enantiomer is reported. The best of the routes investigated for preparation of these enantiomerically pure compounds involves a modification of the Cadiot−Chodkiewicz reaction and the Sharpless asymmetric epoxidation of an (E)-2-ene-4,6-diyn-1-ol as key steps and proceeds in five steps and 18% overall yield. Both enantiomers of nitidon and some related 6-(1,3-diyn-1-yl)-2H-pyran-2-ones have been found to exhibit significant cytotoxic activity against human cancer cell lines in vitro.
Bellina, Fabio; Carpita, Adriano; Mannocci, L.; Rossi, Renzo
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/203842
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