A Facile Method for Monoesterification of α, ω-Dicarboxylic Acids: Application to the Synthesis of Traumatic Acid, A Prostaglandin Synthon

Abstract

During the past decade, methyl 7-(5-oxocyclopentenyl)heptanoate (6) has been frequently used as a key intermediate in prostaglandin synthesis.¹ Although keto ester 6 can be readily obtained by treatment of traumatic acid (5) with polyphosphoric acid followed by esterification with methanolic hydrochloric acid,² this approach is not attractive for large-scale synthesis due to the expense of the latter natural product (5). Recently Salomon and Reuter have reported¹ an alternate route to synthon 6 based on a starting material derived from aleuritic acid, a major component of shellac.