Total Synthesis of (−)-Lamellodysidine A via an Intramolecular Diels–Alder Reaction
Shogo Kamo, Hitomi Kurosawa, Akinobu Matsuzawa, Kazuyuki Sugita
Abstract
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.
Topics & Concepts
Intramolecular forceChemistryDiels–Alder reactionTotal synthesisStereochemistryEnantioselective synthesisSesquiterpeneNatural productCascadeAbsolute configurationOrganic chemistryCatalysisChromatographyMarine Sponges and Natural ProductsSynthetic Organic Chemistry MethodsMicrobial Natural Products and Biosynthesis