Unveiling the Stereochemical Uncertainty of Polyol Scaffolds: Total Synthesis of Mycapolyol E

Mycapolyol E is a cytotoxic metabolite, isolated from the marine sponge Mycale izuensis. After isolation, the stereochemistry of the 1,3-polyol fragment remained uncertain. Aggarwal and coworkers have solved this puzzle in their recent publication in Angewandte Chemie Novit through a combination of total synthesis and nuclear magnetic resonance (NMR). The total synthesis of mycapolyol E was completed in 20 steps, the longest linear sequence, using iterative diboration/homologation reactions as key transformations to assemble the complete carbon backbone with exquisite regio- and stereocontrol (https://doi.org/10.1002/anov.70003).