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EnglishThe 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.
| Autori interni: | |
| Autori: | Bellina, Fabio; Carpita, Adriano; Mannocci, L.; Rossi, Renzo |
| Titolo: | First total synthesis of naturally-occurring (–)-nitidon and its enantiomer |
| Anno del prodotto: | 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. |
| Digital Object Identifier (DOI): | 10.1002/ejoc.200400101 |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
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http://hdl.handle.net/11568/203842
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