np7b00199_si_002.cif (1.25 MB)

Total Synthesis of Tedarene A

Download (1.25 MB)
posted on 02.05.2017, 18:04 by Kelly Maurent, Corinne Vanucci-Bacqué, Nathalie Saffon-Merceron, Michel Baltas, Florence Bedos-Belval
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.