Journal of the American Chemical Society

A novel approach to the synthesis of morphine alkaloids: the synthesis of (d, l)-thebainone-A

MA Tius, MA Kerr

Index: Tius; Kerr Journal of the American Chemical Society, 1992 , vol. 114, # 15 p. 5959 - 5966

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Citation Number: 40

Abstract

Abstract: A nonconventional approach to the preparation of morphinans has been applied to the total synthesis of thebainone-A and 0-thebainone-A. Noteworthy features of this synthesis are the regiospecificity of the Diels-Alder reaction to form 9 and of the enolization- hydroxylation of 11, the unusual aromatization of 14 as well as the selectivity of the intramolecular Michael addition of the amine to form 41. This route offers access to several ...