Total Synthesis of (-)-Lamellodysidine A via an Intramolecular Diets-Alder Reaction

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 Diets-Alder reaction. In addition, single-crystal X-ray crystallographic analysis of the synthetic (-)-lamellodysidine A clearly confirmed the proposed stereo-chemistry and absolute configuration.

Automated summary

In this study, an eight-step enantioselective synthesis of (-)-lamellodysidine A was achieved. The key to the synthesis is a cascade reaction that includes an intramolecular Diets-Alder reaction. Single-crystal X-ray crystallographic analysis of the synthetic (-)-lamellodysidine A confirmed the proposed stereochemistry and absolute configuration.