Enantioselective Synthesis of 15-epi-Haterumalide NA Methyl Ester and Revised Structure of Haterumalide NA

[structure: see text] The enantioselective synthesis of the enantiomer of the haterumalide NA methyl ester, a cytotoxic macrolide from an Okinawan sponge, was achieved from the threitol derivative in 26 steps. The key steps are the stereoselective construction of a chloroolefin unit and the intramolecular Reformatsky-type reaction. This synthesis revised the absolute stereochemistry of haterumalide NA.