Total Synthesis of (-)-Lamellodysidine A via an Intramolecular Diels-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

This study presented a successful eight-step enantioselective synthesis of (-)-lamellodysidine A, a sesquiterpene natural product with a unique tetracyclic skeleton, obtained from a marine sponge. The key to this synthesis is a cascade reaction involving an intramolecular Diels-Alder reaction, and the stereochemistry and absolute configuration were confirmed through single-crystal X-ray crystallography.