Issue 5, 1990

Facile retro Diels–Alder reaction of a pentamethyltricyclo[5.2.1.02,6]decenone derivative: synthesis of (+)-15(S)-prostaglandin A2

Abstract

The incorporation of methyl groups into the C(1), C(7), C(8), C(9), and C(10) positions of tricyclo[5.2.1.02,6]decenone (1) dramatically accelerates the retro Diels–Alder reaction of (3) under Lewis acid catalysis thus permitting access to synthetic natural prostaglandin A2; the X-ray crystal structure of the ammonium salt of (7) is reported.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1990, 410-412

Facile retro Diels–Alder reaction of a pentamethyltricyclo[5.2.1.02,6]decenone derivative: synthesis of (+)-15(S)-prostaglandin A2

P. A. Grieco and N. Abood, J. Chem. Soc., Chem. Commun., 1990, 410 DOI: 10.1039/C39900000410

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