Diels–Alder reaction of furan and fumaryl chloride: X-ray crystal and molecular structure of an oxabicyclo[2.2.1]heptane derivative. Synthesis of reduction products of cis-maneonene-A

Abstract

The addition of fumaryl chloride to furan, followed by hydrolysis and bromolactonisation of the adduct, leads to the bromo-lactone acid (2a) which serves as a precursor for the synthesis of the reduction products (5a), (5b), and (6a) of cis-maneonene-A and of the tosylate (6b) whose X-ray crystal structure has been determined.