Synthesis of (.+-.) cervinomycins A1 and A2

TR Kelly, CT Jagoe, Q Li

Index: Kelly, T. Ross; Jagoe, Christopher T.; Li, Qun Journal of the American Chemical Society, 1989 ,  vol. 111,  # 12  p. 4522 - 4524

Full Text: HTML

Citation Number: 52

Abstract

Annelation of the oxazolidine ring onto 13 proved more difficult than expected. Reaction of 13 with ethanolamine proceeds smoothly to give 14, but all efforts at acid-catalyzed cyclodehydration of 14 led to isoquinoline 16 (Scheme 111). Attempts at cyclizing 16 to 15 failed. Mechanistic considerations eventually provided an avenue for redress. In particular, all the failed methods-which rely on conventional routes to oxazolidinespresumably share ...