Premium
Synthesis and Biological Evaluation of Bromo‐ and Fluorodanicalipin A
Author(s) -
Fischer Stefan,
Huwyler Nikolas,
Wolfrum Susanne,
Carreira Erick M.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201510608
Subject(s) - lipophilicity , halogen , chemistry , molecule , stereochemistry , combinatorial chemistry , computational chemistry , organic chemistry , alkyl
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.