Preparation of 2,6-Dioxabicyclo[3.3.0]octan-3,7-dione and Its Application to the Synthesis of (±)-Eldanolide

Abstract

2,6-Dioxabicyclo[3.3.0]octan-3,7-dione seems to be a promising compound for the synthesis of natural products such as epoxyeicosatrienoic acid, laurediol, and eldanolide. This compound, consisting of two 7-lactones, could be prepared by double lactonization of the silver salt of trans-3-hexenedioic acid using iodine. Starting with this bis-lactone, (+)-eldanolide could be synthesized in a stereocontrol led manner. © 1988, The Pharmaceutical Society of Japan. All rights reserved.