Synthetic approach toward the structural elucidation of symbiodinolide: Stereodivergent synthesis and stereostructural revision of the C79-C104 fragment

Stereoselective synthesis of the proposed C79-C104 fragment of symbiodinolide, a polyol marine natural product, revealed that the stereochemistry of the C91-C99 carbon chain domain of this natural product needs to be reassigned. Next, stereodivergent synthesis of eight possible diastereomers corresponding to the C79-C97 and C94-C104 fragments resulted in the proposal of two candidate stereostructures, respectively. The synthesis of four candidate compounds of the C79-C104 fragment and comparison of their ¹³ C NMR data with those of the natural product allowed stereostructural revision of this fragment of symbiodinolide.