Acta Cryst. (2003). E59, o114-o116  [ doi:10.1107/S1600536802023413 ]

5-Butylthevinone: stereochemistry of the Diels-Alder reaction of 5-butylthebaine with 3-buten-2-one

W. Chen, M. D. Metcalf, A. Coop, J. L. Flippen-Anderson and J. R. Deschamps

Abstract: In this paper, we report on the X-ray analysis of 5-butylthevinone (7-acetyl-4,5-epoxy-3,6-dimethoxy-5-butyl-17-methyl-6,14-ethenoisomorphinan), C₂₇H₃₅NO₄. This compound is the sole product of a Diels-Alder reaction of 5-butylthebaine with 3-buten-2-one, through attack of the dienophile on the -face of the diene, even though it has been suggested that the introduction of 5-substituents tends to hinder attack from the -face, and leads to the production of exo-etheno adducts through attack from the -face.

Online 10 January 2003

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