High pressure organic chemistry. Part 17. Diels–Alder reaction of methyl palustrate with maleic anhydride and N-phenylmaleimide

Abstract

Diels–Alder reactions of methyl palustrate with a variety of dienophiles have been investigated under high pressure conditions. Thus, on reaction with maleic anhydride the adducts 5(19%) and 6(8%) are produced and with N-phenylmaleimide compound 7(68%) is obtained. The structures and relative stereochemistry of these unprecedented adducts, 5 and 7, are established on the basis of spectral analysis (mainly 2D NMR) and X-ray diffraction.