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Synthesis from d -Altrose of (5 R ,6 R ,7 R ,8 S )-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

✍ Scribed by Araújo, Noelia; Jenkinson, Sarah F.; Martínez, R. Fernando; Glawar, Andreas F. G.; Wormald, Mark R.; Butters, Terry D.; Nakagawa, Shinpei; Adachi, Isao; Kato, Atsushi; Yoshihara, Akihide; Akimitsu, Kazuya; Izumori, Ken; Fleet, George W. J.


Book ID
111964348
Publisher
American Chemical Society
Year
2012
Tongue
English
Weight
612 KB
Volume
14
Category
Article
ISSN
1523-7060

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A stereoselective synthesis of 1,4-dideoxy-1,4-imino-D-allitol 1 and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline was achieved via the addition of vinylmagnesium bromide to the benzylimine derived from (R)-2,3-O-isopropylidene glyceraldehyde followed by N-allylation, ring-closing metathesis (