Structure and absolute stereochemistry of stolonoxide A, a novel cyclic peroxide from the marine tunicate Stolonica socialis

Stolonoxide A, a novel peroxide possessing an unprecedented molecular arrangement, has been isolated as its methyl ester from the marine tunicate Stolonica socialis. The structure of stolonoxide A has been fully elucidated by spectroscopic methods and its relative stereochemistry secured by chemical conversion. The absolute stereochemistry is suggested on the basis of Mosher’s method on the diol derivative obtained by hydrogenation of the natural product.