TY - JOUR
T1 - A divergent route to 3-amino-2,3,6-trideoxysugars including branched sugar
T2 - Synthesis of vancosamine, daunosamine, saccharosamine, and ristosamine
AU - Doi, Takayuki
AU - Shibata, Kazuaki
AU - Kinbara, Atsushi
AU - Takahashi, Takashi
PY - 2007/11/5
Y1 - 2007/11/5
N2 - Four 3-amino-2,3,6-trideoxysugars were synthesized by a divergent route from a single enone 9a. The Migita-Stille coupling introduced a methyl group at the 3-position. Stereoselective reduction of enone and the Mitsunobu reaction provided both β- and α-hydroxy groups at the 4-position. Stereospecific radical cyclization of the C4 carbamoyl moiety furnished the desired 5a, 5b and 6a, 6b, respectively.
AB - Four 3-amino-2,3,6-trideoxysugars were synthesized by a divergent route from a single enone 9a. The Migita-Stille coupling introduced a methyl group at the 3-position. Stereoselective reduction of enone and the Mitsunobu reaction provided both β- and α-hydroxy groups at the 4-position. Stereospecific radical cyclization of the C4 carbamoyl moiety furnished the desired 5a, 5b and 6a, 6b, respectively.
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U2 - 10.1246/cl.2007.1372
DO - 10.1246/cl.2007.1372
M3 - Article
AN - SCOPUS:36849012980
SN - 0366-7022
VL - 36
SP - 1372
EP - 1373
JO - Chemistry Letters
JF - Chemistry Letters
IS - 11
ER -