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

被引：47

作者：

Bellina, F ^{[1
]}

Carpita, A ^{[1
]}

Mannocci, L ^{[1
]}

Rossi, R ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 12期

关键词：

antitumour agents; C-C coupling; lactones; natural products; synthetic methods;

D O I：

10.1002/ejoc.200400101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

引用

页码：2610 / 2619

页数：10

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