Cyclization of Aminocyclopropanes in Indole Alkaloids Synthesis

被引：27
|
作者：
De Simone, Filippo [1 ]
Waser, Jerome [1 ]
机构：
[1] Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, EPFL SB ISIC LCSO BCH 4306, CH-1015 Lausanne, Switzerland
来源：
SYNLETT | 2011年 / 05期
关键词：
alkaloids; cyclization; indoles; iminium; aminocyclopropanes; ACCEPTOR-SUBSTITUTED CYCLOPROPANES; DIVERSITY-ORIENTED SYNTHESIS; NAZAROV CYCLIZATION; ORGANIC-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; KETONES; DONOR; RING; 2-(1,3-DITHIAN-2-YL)INDOLES; CYCLOADDITION;
D O I：
10.1055/s-0030-1259553
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The regioselective and diastereoselective cyclization of acyliminium intermediates generated from aminocyclopropanes on unprotected indoles is presented. The recent results obtained in our group are compared with previous intermolecular reactions with aminocyclopropanes as well as with other cyclization methods involving iminium ions and unprotected indoles. A first speculative analysis of possible reaction mechanisms allows rationalizing the observed selectivity. The high potential of the method for the synthesis of natural alkaloids is demonstrated in the formal synthesis of aspidospermidine and the total synthesis of goniomitine.
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页码：589 / 593
页数：5
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