Rational design of templates for intramolecular O, N-acyl transfer via medium-sized cyclic intermediates derived from L-cysteine. Definition of an experimental …

…, JC Dewan, NG Galakatos, D Kerkman…

Index: Kemp, D. S.; Carey, Robert I.; Dewan, John C.; Galakatos, Nicholas G.; Kerkman, Daniel; Leung, See-Lap Journal of Organic Chemistry, 1989 , vol. 54, # 7 p. 1589 - 1603

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Citation Number: 29

Abstract

Rate constants and effective molarities for intramolecular 0, N-acyl transfer have been measured for a series of unsymmetrical disulfides derived from cysteine and having the general structure H-Cys (S-XY-0Ac)-OMe, for which XY is a rigid molecular spacing element that maintains a fixed OS distance lying in the range of 4.5-6.5 A. A synthetic route is described to 4-hydroxy-6-mercaptodibenzothiophene, involving lithiation of 4- ...