Tetrahedron

Total synthesis of antitumor agent at-125,(αS, 5S)-α-amino-3-chloro-4, 5-dihydro-5-isoxazoleacetic acid

JE Baldwin, JK Cha, LI Kruse

Index: Baldwin, Jack E.; Cha, Jin K.; Kruse, Lawrence I. Tetrahedron, 1985 ,  vol. 41,  # 22  p. 5241 - 5260

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Citation Number: 29

Abstract

A short and efficient total synthesis of racemic AT-125 and its racemic threo isomer proceeds via an intramolecular Michael cyclization of a protected α, β-dehydroglutamic acid γ- hydroxamate. Separation of diastereomers and deprotection to racemic AT-125 followed by enzymatic resolution of the N-chloroacetamide with hog-kidney acylase provides the natural αS, 5S isomer.