1. Total Synthesis of Tedarene A.
- Author
-
Maurent K, Vanucci-Bacqué C, Saffon-Merceron N, Baltas M, and Bedos-Belval F
- Subjects
- Animals, Diarylheptanoids chemistry, Molecular Structure, Propanols chemistry, Stereoisomerism, Diarylheptanoids chemical synthesis, Diarylheptanoids isolation & purification, Ethers chemistry, Porifera chemistry, Propanols chemical synthesis
- 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.
- Published
- 2017
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