Enamino ester reduction:: A short enantioselective route to pyrrolizidine and indolizidine alkaloids.: Synthesis of (+)-laburnine, (+)-tashiromine, and (-)-isoretronecanol

被引:117
作者
David, O [1 ]
Blot, J [1 ]
Bellec, C [1 ]
Fargeau-Bellassoued, MC [1 ]
Haviari, G [1 ]
Célérier, JP [1 ]
Lhommet, G [1 ]
Gramain, JC [1 ]
Gardette, D [1 ]
机构
[1] Univ Paris 06, UMR 7611, Lab Chim Heterocycles, F-75252 Paris 05, France
关键词
D O I
10.1021/jo982169p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various chiral pyrrolidine tetrasubstituted beta-enamino esters were reduced catalytically or chemically with good to moderate diastereoselectivity owing to a chiral induction originated from (S)-alpha-methylbenzylamine. With endocyclic double bond compounds, the best result was obtained using PtO2 as hydrogenation catalyst and led to a major syn addition product (e.d. 90%). In the case of exocyclic double bond compounds, hydrogenation over Pd/C gave rise to the higher diastereoselectivity and mainly afforded the unexpected anti addition product (e.d. 84%). The scope of these reductions has been extended to the synthesis of three pyrrolizidine or indolizidine alkaloids: (+)-tashiromine, (+)-laburnine, and (-)-isoretronecanol. Syntheses of these natural products, starting from chiral beta-enamino diesters, were achieved in a short and convenient manner, leading to enantiopure compounds in good overall yields.
引用
收藏
页码:3122 / 3131
页数:10
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