Total Synthesis of (+)-Sarcophytin.
Leonardo J NanniniSuren J NematErick M CarreiraPublished in: Angewandte Chemie (International ed. in English) (2017)
A total synthesis of the cembranoid (+)-sarcophytin is presented, featuring a Diels-Alder cycloaddition of an enone as the dienophile with an ester-derived dienoate. The study highlights a peculiar geometric preference for the Z dienoate to furnish the cycloadduct. The endgame involves a reaction cascade, including lactone opening, alcohol oxidation, and ketone epimerization to complete an efficient synthesis. A salient feature of the synthesis is the resulting reassignment of the absolute configuration, which corrects the previously reported nominal structure.