title: 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.
authors: Laboratorium für Organische Chemie, ETH Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
authors: Stefan
authors: S
authors: Fischer
authors: Laboratorium für Organische Chemie, ETH Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
authors: Nikolas
authors: N
authors: Huwyler
authors: Laboratorium für Organische Chemie, ETH Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
authors: Susanne
authors: S
authors: Wolfrum
authors: Laboratorium für Organische Chemie, ETH Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland. carreira@org.chem.ethz.ch.
authors: Erick M
authors: http://orcid.org/0000-0003-1472-490X
authors: EM
authors: Carreira
mesh_terms: D001966:Bromine / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D005461:Fluorine / Q000737:chemistry*; D008055:Lipids / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D008055:Lipids; D005461:Fluorine; D001966:Bromine
keywords: bromine; chlorosulfolipids; conformational analysis; fluorine; natural products; total synthesis