Synthesis of the DE-ring of goniodomin A and prediction of its natural relative stereochemistry

Goniodomin A (1) was first isolated from Alexandrium hiranoi as a stereochemically unidentified antifungal agent in 1987 by Murakami. In this study, two stereoisomeric series of non-macrocyclic and macrocyclic DE-ring model compounds of 1 were synthesized, and the natural relative stereochemistry of the DE-ring was predicted by NMR comparison of 1 with these model compounds.