Total Synthesis of Tedarene A

Kelly Maurent (1) , Corinne Vanucci-Bacqué (1) , Nathalie Saffon-Merceron (2) , Michel Baltas (1) , Florence Bedos-Belval (1)

1 SPCMIB - Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique
2 ICT - Institut de Chimie de Toulouse

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.

Mots clés: Mixtures; Hydrocarbons; Aromatic compounds; Alcohols; Aldehydes

Domaines: Chimie

Kelly Maurent, Corinne Vanucci-Bacqué, Nathalie Saffon-Merceron, Michel Baltas, Florence Bedos-Belval. Total Synthesis of Tedarene A. Journal of Natural Products, 2017, 80 (5), pp.1623-1630. ⟨10.1021/acs.jnatprod.7b00199⟩. ⟨hal-02444243⟩