Intramolecular O, N-acyl transfer via cyclic intermediates of nine and twelve members. Models for extensions of the amine capture strategy for peptide synthesis

DS Kemp, DJ Kerkman, SL Leung…

Index: Kemp, D. S.; Kerkman, Daniel J.; Leung, See-Lap; Hanson, Gunnar Journal of Organic Chemistry, 1981 , vol. 46, # 3 p. 490 - 498

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Citation Number: 27

Abstract

N-(2-acetoxybenzyl)-2-aminoacetate, methyl N-[(8-acetoxy-l-naphthyl) methylene]-2- aminoacetate and their alanine and valine analogues in acetonitrile, Me2S0, and other solvents. Synthesis of these substrates is described, and a novel two-step synthesis is reported of 4-hydroxy-5-formylxanthene from 2, 3-diacetoxybenzaldehyde and 2- (isopropoxymethylene) cyclohexanone in 29% yield. Facile intramolecular acyl transfer ...