Synthesis and Biological Evaluation of Bromo- and Fluorodanicalipin A

Abstract

We disclose the syntheses of (+)-bromodanicalipin A as well as (±)-fluorodanicalipin A. The relative configuration and ground-state conformation in solution of both molecules was secured by J-based configuration analysis which revealed that these are identical to natural danicalipin A. Furthermore, preliminary toxicological investigations suggest that the adverse effect of danicalipin A may be due to the lipophilicity of the halogens.

Keywords: bromine; chlorosulfolipids; conformational analysis; fluorine; natural products; total synthesis.