posted on 2022-12-12, 19:06authored byHarry
B. Hicks, Daniel S. Brown, Hau Sun Sam Chan, Bruno A. Sousa, Kirsten E. Christensen, Jonathan W. Burton
The (E/Z)-ocellenynes
are C15 dibrominated Laurencia natural
products
whose structures have been subject to several reassignments on the
basis of extensive NMR analysis, biosynthetic postulates, and DFT
calculations. Herein, we report the synthesis of both (E)- and (Z)-ocellenyne, which, in combination with
single crystal X-ray diffraction studies, allows their absolute configuration
to be established and defines the configuration of the syn-12,13-dibromide as being (S, S) in keeping with their proposed biogenesis from the (6S, 7S)-laurediols.