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Paper | Regular issue | Vol 55, No. 6, 2001, pp.1029-1043
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9177
A Formal Synthesis of (±)-Eseroline via an Azaoxy-Cope Rearrangement

Paulo F. Santos, Paulo S. Almeida, Ana M. Lobo,* and Sundaresan Prabhakar*

*Chemistry Department, Center for Fine Chemistry and Biotechnology, Faculty of Sciences and Technology, New University of Lisbon, 2825-114 Monte de Caparica, Portugal

Abstract

A novel synthesis of (±)-desoxyeseroline, from the crucial oxindole (15), obtained by a 3,3-sigmatropic rearrangement of the enolate derived from the hydroxamic acid derivative (5) followed by radical desulfurisation, has been described. The requisite C2N fragment has been introduced through a Michael addition of nitroethylene to 15.