Tetrahedron letters

Synthesis of an analogue of lavendamycin and of conformationally restricted derivatives by cyclization via a hemiaminal intermediate

A Nourry, S Legoupy, F Huet

Index: Nourry, Arnaud; Legoupy, Stephanie; Huet, Francois Tetrahedron Letters, 2007 , vol. 48, # 34 p. 6014 - 6018

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Citation Number: 23

Abstract

Quinoline 12 was obtained by a Friedländer reaction from 2-aminobenzaldehyde and methyl acetoacetate. Reduction, silylation then oxidation provided compound 8a. A Pictet– Spengler reaction between the latter and tryptophan methyl ester yielded compound 14, then compound 7 by desilylation. Numerous attempts to prepare a cyclized derivative of this analogue of lavendamycin 7 by conventional ways failed. Fortunately, a good result was ...