Total synthesis of nocardicin A. Synthesis of 3-ANA and nocardicin A

GA Koppel, L McShane, F Jose…

Index: Koppel,G.A. et al. Journal of the American Chemical Society, 1978 , vol. 100, p. 3933 - 3935

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Citation Number: 45

Abstract

Figure 1. chiral starting materials. We chose r-cysteine and Dp-hydroxyphenylglycine. The construction of the crucial 6-lactam ring requires the bond-forming reactions shown in Figure I. The bond formation between the a-amino group of Dphydroxyphenylglycine and the carboxyl of L-cysteine was a relatively trivial amide group synthesis. However, the second bond formation, that of the amino group to C-4 while retaining the chirality at C-3, ...