Total Syntheses and Structural Revision of Menominins A and B.

This work reports the stereoselective total synthesis and structural revision of menominins A (1) and B (2) featuring a 3,8-dihydroxy-2-methyltetradecanoic acid residue with a (2R,3R,8S) configuration as a key stereochemical element. This strategy features Evans aldol reactions, Mitsunobu inversion, and ring-closing metathesis as the key steps. Extensive analysis of the spectral data for the synthetic material, combined with reported data, led to structural revisions of menominins A (1) and B (2).