Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars.
Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-d-mannitol) was the acetonation of d-mannose.
Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. yucy@iccas.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, China.
Bao-Chen
BC
Qian
Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan. kato@med.u-toyama.ac.jp.
Akiko
A
Kamori
Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan. kato@med.u-toyama.ac.jp.
Kyoko
K
Kinami
Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan. kato@med.u-toyama.ac.jp.
Atsushi
A
Kato
Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. yucy@iccas.ac.cn.
Yi-Xian
YX
Li
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK and National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, PR China.
George W J
GW
Fleet
Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. yucy@iccas.ac.cn and National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, PR China.
Chu-Yi
CY
Yu
D002236:Carbohydrate Conformation; D060326:Chemistry Techniques, Synthetic; D008958:Models, Molecular; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D000073893:Sugars / Q000138:chemical synthesis* / Q000737:chemistry*; D017026:Swainsonine / Q000138:chemical synthesis* / Q000737:chemistry*
D011759:Pyrrolidines; D000073893:Sugars; C032519:pyrrolidine; D017026:Swainsonine