Tetrahedron

Indole as a tool in synthesis. Indolenine approach to 4, 5-epoxy-10-normorphinans

…, S Dridi, J Laronze, F Sigaut, D Patigny, JY Laronze…

Index: Sapi, Janos; Dridi, Seloua; Laronze, Jacqueline; Sigaut, Francoise; Patigny, Dominique; Laronze, Jean-Yves; Levy, Jean; Toupet, Loic Tetrahedron, 1996 , vol. 52, # 24 p. 8209 - 8222

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Citation Number: 9

Abstract

The 4, 5-epoxy-10-normorphinans 2a and 2b featuring the morphine skeleton lacking the B- ring were synthesized using the “nitrous acid deamination” of indolenines as the key step. Thus, indolenines 13 and 15 were prepared by Fischer synthesis from the corresponding bicyclic ketolactams 6 and 12, respectively, and further transformed into the related hexahydrodibenzofurans. Ketolactam 6 was obtained from 3-nitromethylcyclohexanone ...