A practical approach to the fused β-carboline system. asymmetric synthesis of indolo [2, 3-a] indolizidinones via a diastereoselective intramolecular α-amidoalkylation …

A Ardeo, E Garcı́a, S Arrasate, E Lete, N Sotomayor

Index: Ardeo, Ainhoa; Garcia, Eva; Arrasate, Sonia; Lete, Esther; Sotomayor, Nuria Tetrahedron Letters, 2003 , vol. 44, # 46 p. 8445 - 8448

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Citation Number: 32

Abstract

Fused β-carboline systems, as indolo [2, 3-a] indolizidinones, indolo [2, 3-a] quinolizidinones, their 2-oxa analogues, and benzo [a] indolo [2, 3-a] indolizidinones are prepared efficiently via an RLi addition-N-acyliminium ion cyclisation sequence on readily available imides. In an enantioselective variant of these α-amidoalkylation reactions, the addition of MeLi to a chiral non-racemic imide derived from tryptophan yielded an oxo ...