Synthetic approaches to amino analogues of N-acetylcolchinol.
A straightforward synthesis of aminodibenzoxepines, new analogues of N-acetylcolchinol, is reported by using two different strategies. The first strategy involves a Grignard addition, a biaryl Suzuki-Miyaura coupling, and a HF-mediated cyclodehydration as key steps. A second strategy, better adapted to the synthesis of analogues bearing a benzylic substituent, was designed by inverting the order of the Grignard addition and the biaryl coupling. This allowed the rapid and reliable production of a series of substituted aminodibenzoxepines. A chelate model was proposed to account for the diastereoselectivity observed in the Grignard addition step.
Colombel
Virginie
V
Université Lyon 1, CNRS UMR5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, 43 Boulevard du 11 Novembre 1918, 69622 Villeurbanne, France.
Baudoin
Olivier
O
D000588:Amines / Q000138:chemical synthesis; D001584:Benzoxepins / Q000138:chemical synthesis; D003078:Colchicine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D020650:Combinatorial Chemistry Techniques; D008722:Methods
D000588:Amines; D001584:Benzoxepins; C017815:N-acetylcolchinol; D003078:Colchicine