Synthesis of 4-amino-2 (5H)-furanones through intra-and intermolecular nitrile addition of ester enolates. Construction of carbon framework of an antitumor antibiotic …

T Hiyama, H Oishi, Y Suetsugu, K Nishide…

Index: Hiyama; Oishi; Suetsugu; et al. Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 6 p. 2139 - 2150

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Citation Number: 28

Abstract

Two new routes to 4-amino-2 (5H)-furanones are disclosed. The one is based on the reaction of a magnesium enolate of t-butyl acetate or propionate with O-protected cyanohydrins followed by acid-treatment which effects hydrolysis of the ester group, deprotection, olefin isomerization and lactonization all in a single operation. The other is base-induced ringclosure of α-acyloxy nitriles. The two methods are applied to ...