New access to indolizidine and pyrrolizidine alkaloids from an enantiopure proline:: Total syntheses of (-)-lentiginosine and (1R,2R,7aR)-Dihydroxypyrrolizidine

被引：39
作者：
Angle, Steven R. [1 ]
Bensa, David [1 ]
Belanger, Dominique S. [1 ]
机构：
[1] Univ Calif Riverside, Dept Chem, Riverside, CA 92521 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 15期
关键词：
D O I：
10.1021/jo070462w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new approach to the synthesis of indolizidine and pyrrolizidine skeletons is reported. (-)-Lentiginosine and (1R,2R,7aR)-dihydroxypyrrolizidine have both been synthesized in 13 steps from di-O-isopropylidene-D-mannitol. The common key intermediate is (-)-dihydroxyproline benzyl ester 10.
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页码：5592 / 5597
页数：6
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