Construction of Hydroxylated Alkaloids (.+-.)-Mannonolactam,(.+-.)-Deoxymannojirimycin, and (.+-.)-Prosopinine through Aza-Annulation

GR Cook, LG Beholz, JR Stille

Index: Cook, Gregory R.; Beholz, Lars G.; Stille, John R. Journal of Organic Chemistry, 1994 , vol. 59, # 13 p. 3575 - 3584

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Citation Number: 142

Abstract

The aza-annulation ofj3-enamino carbonyl substrates with acrylate derivatives provides an efficient and convenient route for the regioselective construction of 8-lactams. This two-step ring-forming sequence involved initial generation of the benzyl enamine through either a condensation or conjugate addition reaction with BnNHz, followed by aza-annulation with acryloyl chloride or acrylic anhydride. Controlled by the rigid framework of the ...