Pyrrolizidine alkaloids by intramolecular palladium-catalysed allylic alkylation:: Synthesis of (±)-isoretronecanol

被引：33
作者：
Lemaire, S
Giambastiani, G
Prestat, G
Poli, G
机构：
[1] Univ Paris 06, UMR 7611 CNRS, Chim Organ Lab, F-75252 Paris, France
[2] CNR, ICCOM, Inst Chem Organomet Cpds, Florence Res Area, I-50019 Florence, Italy
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 13期
关键词：
alkaloids; allylic alkylation; palladium; synthetic methods;
D O I：
10.1002/ejoc.200400135
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and stereo convergent approach to 3-substituted hexahydroindol-2-one derivatives by palladium-catalysed intramolecular allylic alkylation has been developed. Subsequently, the straightforward conversion of the hexahydroindol-2-one 7d into the alkaloid (+/-)-isoretronecanol has been performed. The synthesis entails 11 steps starting from 1,3-cyclohexadiene, affording the final target in a 29% overall yield. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
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收藏
页码：2840 / 2847
页数：8
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