Tetrahedron: Asymmetry

Synthesis of (2R, 5S)-and (2S, 5S)-2-carboxy-1, 4-diaza-[4.3. 0] bicyclononane as building blocks for the synthesis of new potential HIV protease inhibitors

M Falorni, A Porcheddu, G Giacomelli

Index: Falorni, Massimo; Porcheddu, Andrea; Giacomelli, Giampaolo Tetrahedron Asymmetry, 1996 , vol. 7, # 7 p. 1999 - 2005

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Citation Number: 11

Abstract

A procedure for the preparation of optically active (2R, 5S)-and (2S, 5S)-2-Carboxy-1, 4- diaza-[4.3. 0] bicyclononane is described. The method is based on the reduction of diketopiperazines obtained from cyclization of Pro-L-Ser or Pro-D-Ser and occurs without loss of enantiomeric purity. The synthesis is based on readily available starting materials and can be easily arranged for multigram scale preparations.

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