Synthesis from d-Altrose of (5R,6R,7R,8S)-5,7-Dihydroxy-8-hydroxymethylconidine and 2,4-Dideoxy-2,4-imino-d-glucitol, Azetidine Analogues of Swainsonine and 1,4-Dideoxy-1,4-imino-d-mannitol

Noelia Araújo, Sarah F. Jenkinson, R. Fernando Martínez, Andreas F. G. Glawar, Mark R. Wormald, Terry D. Butters, Shinpei Nakagawa, Isao Adachi, Atsushi Kato, Akihide Yoshihara, Kazuya Akimitsu, Ken Izumori, and George W. J. Fleet. Synthesis from d-altrose of (5R,6R,7R,8S)-5,7-dihydroxy-8-hydroxymethylconidine and 2,4-dideoxy-2,4-imino-d-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-d-mannitol, Org. Lett., 2012, 14, 4174–4177. doi: 10.1021/ol301844n.

Abstract

Ring closure of a 3,5-di-O-triflate derived from d-altrose with benzylamine allowed the formation of both monocyclic and bicyclic azetidine analogues of swainsonine.