Synthesis of Novel Tetrahydropyran‐Based Dipeptide Isosters by Overman Rearrangement of 2,3‐Didehydroglycosides

Abstract

Abstract Differently functionalized tetrahydropyran‐based dipeptide isosters have been efficiently synthesized from 3,4,6‐tri‐ O ‐acetyl‐ D ‐glucal. Analogues of the hsp65 p2−13 epitope of Mycobacterium tuberculosis and Mycobacterium leprae were prepared by replacement of the Ala−Tyr or Glu−Glu moiety in the native dodecapeptide with the prepared dipeptide isosters. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)