The Journal of organic chemistry

Synthesis of an optically active, bicyclic 2-pyridone dipeptide mimetic

PS Dragovich, R Zhou, TJ Prins

Index: Dragovich, Peter S.; Zhou, Ru; Prins, Thomas J. Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 741 - 746

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Citation Number: 20

Abstract

The eleven-step preparation of the bicyclic 2-pyridone dipeptide mimetic 1 [(3 S)-6-( benzyloxycarbonylamino)-5-oxo-1, 2, 3, 5-tetrahydroindolizine-3-carboxylic acid] in optically active form (60% ee) is described. Key steps in the synthesis of 1 include the osmium- catalyzed asymmetric dihydroxylation of olefin 13 [(6-but-3-enyl-2-methoxypyridin-3-yl) carbamic acid benzyl ester] and the intramolecular cyclization of protected diol 19 [(3'R)-{6 ...