Tetrahedron: Asymmetry

Synthesis of thienamycin-like 2-iso-oxacephems with optional stereochemistry

Z Sánta, J Nagy, J Nyitrai

Index: Santa, Zsuzsanna; Nagy, Jozsef; Nyitrai, Jozsef Tetrahedron Asymmetry, 2006 , vol. 17, # 22 p. 3111 - 3127

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Citation Number: 7

Abstract

All four trans-stereoisomers of 7-(1-hydroxyethyl)-2-iso-oxacephem-4-carboxylic acids, which are the 2-iso-oxacephem analogues of Thienamycin, have been synthesized.(αR, 6R, 7R)-and (αS, 6S, 7S)-7-(1-hydroxyethyl)-3-methyl-2-iso-oxacephem-4-carboxylic acids have been prepared starting from l-and d-threonine, the configuration at the α-position was inverted by using Mitsunobu reactions providing the (αS, 6R, 7R)-and (αR, 6S, 7S)- ...