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.
Kigoshi
Hideo
H
Department of Chemistry, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan. kigoshi@chem.tsukuba.ac.jp
Kita
Masaki
M
Ogawa
Seiji
S
Itoh
Masahiro
M
Uemura
Daisuke
D