Palladium(II)-catalyzed cyclization of urethanes and total synthesis of 1-deoxymannojirimycin.
The palladium(II)-catalyzed cyclization of the urethane 8, which was derived from D-mannitol, gave the cyclic compound 9 with excellent diastereoselectivity. During these transformations, the Pd(II) species are not reduced and thus the catalyst can recycle without its reoxidation. The cycloadduct 9 was converted to 1-deoxymannojirimycin.
Yokoyama
H
H
Department of Chemistry, Faculty of Science, Toyama University, 3190 Gofuku, Toyama 930-8555, Japan. hirai@sci.toyama-u.ac.jp
Otaya
K
K
Kobayashi
H
H
Miyazawa
M
M
Yamaguchi
S
S
Hirai
Y
Y
D017485:1-Deoxynojirimycin / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D010165:Palladium; D014520:Urethane / Q000737:chemistry*
D007202:Indicators and Reagents; D017485:1-Deoxynojirimycin; D014520:Urethane; D010165:Palladium