特达瑞烯A的全合成

Total Synthesis of Tedarene A.

作者信息

Maurent Kelly, Vanucci-Bacqué Corinne, Saffon-Merceron Nathalie, Baltas Michel, Bedos-Belval Florence

机构信息

UMR CNRS 5068, LSPCMIB, Université Paul Sabatier , 118 Route de Narbonne, Toulouse, 31062 Cedex 9, France.

Institut de Chimie de Toulouse, ICT FR 2599, Université Paul Sabatier , Toulouse III, Toulouse 31062 Cedex 9, France.

出版信息

J Nat Prod. 2017 May 26;80(5):1623-1630. doi: 10.1021/acs.jnatprod.7b00199. Epub 2017 May 2.

DOI:10.1021/acs.jnatprod.7b00199

PMID:28463511

Abstract

Tedarene A is a macrocyclic diaryl ether heptanoid isolated from the marine sponge Tedania ignis showing an inhibitory effect against nitric oxide production. The first total synthesis of tedarene A was achieved starting from the commercially available 3-(4-methoxyphenyl)propan-1-ol in nine steps and 15.3% overall yield. The synthetic sequence featured an E,Z-dienic bond introduction and a macrocyclization under Ullman conditions. During the synthesis, the E,E-isomer of tedarene A was also obtained and fully characterized.

摘要

特达雷烯A是一种从海洋海绵火焰特达海绵中分离出的大环二芳基醚庚烷类化合物，对一氧化氮的产生具有抑制作用。特达雷烯A的首次全合成是从市售的3-(4-甲氧基苯基)丙-1-醇开始，经过九步反应，总收率为15.3%。合成路线的特点是引入E,Z-二烯键并在乌尔曼条件下进行大环化反应。在合成过程中，还获得了特达雷烯A的E,E-异构体并对其进行了全面表征。