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Total Synthesis of (-)-Lamellodysidine A via an Intramolecular Diels-Alder Reaction. 2022
Department of Synthetic Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo, 142-8501, Japan.
In this study, we achieved an eight-step enantioselective synthesis of (-)-lamellodysidine A, a structurally intriguing sesquiterpene natural product featuring a 5/5/6/6-fused tetracyclic skeleton that was obtained from the marine sponge Lamellodysidea herbacea. The key to the synthesis is a cascade reaction that includes an intramolecular Diels-Alder reaction. In addition, single-crystal X-ray crystallographic analysis of the synthetic (-)-lamellodysidine A clearly confirmed the proposed stereochemistry and absolute configuration.
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