Stereochemical Revision, Total Synthesis, and Solution State Conformation of the Complex Chlorosulfolipid Mytilipin B

Abstract

Chlorosulfolipids constitute a structurally intriguing and synthetically challenging class of marine natural products that are isolated from mussels and freshwater algae. The most complex structure from this family of compounds is currently represented by Mytilipin B, isolated in 2002 from culinary mussel Mytilus galloprovincialis, whose initially proposed structure was shown to be incorrect. In this study, we present the synthesis of four diastereomers which allowed the reassignment of eight stereocenters and the stereochemical revision of Mytilipin B, along with the determination of the dominant solution-state conformation.