Synthesis and Biological Evaluation of Bromo- and Fluorodanicalipin A

被引：37

作者：

Fischer, Stefan ^{[1
]}

Huwyler, Nikolas ^{[1
]}

Wolfrum, Susanne ^{[1
]}

Carreira, Erick M. ^{[1
]}

机构：

[1] ETH, Organ Chem Lab, HCI H335 Vladimir Prelog Weg 3, CH-8093 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 07期

基金：

欧洲研究理事会;

关键词：

bromine; chlorosulfolipids; conformational analysis; fluorine; natural products; total synthesis; ACYCLIC ALLYLIC ALCOHOLS; BETA-HYDROXY KETONES; OCHROMONAS-DANICA; ABSOLUTE-CONFIGURATION; COUPLING-CONSTANTS; SECONDARY ALCOHOLS; NATURAL-PRODUCTS; IN-VIVO; CHLOROSULFOLIPIDS; BIOSYNTHESIS;

D O I：

10.1002/anie.201510608

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We disclose the syntheses of (+)-bromodanicalipin A as well as (o)-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 danicalipinA may be due to the lipophilicity of the halogens.

引用

页码：2555 / 2558

页数：4

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