Synthesis of (±)-nephromopsinic acid

Abstract

The preparation of (±)-nephromopsinic acid form 7-oxabicyclo[2.2.1]hept-5-en-2-one is reported. The synthesis takes advantage of a previously reported radical acyl migration. A remarkable iodide mediated cleavage of the bicyclic systems followed by the introduction of the γ-chain via a mixed Kolbe electrolysis are the key features of this approach. This strategy is expected to be of interest for the preparation of all kinds of paraconic acids with excellent control of the stereochemistry.