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.
Université Lyon 1, CNRS UMR5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, 43 Boulevard du 11 Novembre 1918, 69622 Villeurbanne, France.
Virginie
V
Colombel
Olivier
O
Baudoin
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