Concise synthesis of 1-epi-castanospermine

被引：5
作者：
Cheng, Bin [1 ,2 ]
Li, Yi-Xian [1 ,2 ]
Jia, Yue-Mei [1 ,2 ]
Yu, Chu-Yi [1 ,2 ,3 ]
机构：
[1] Chinese Acad Sci, Inst Chem, CAS Res Educ Ctr Excellence Mol Sci, CAS Key Lab Mol Recognit & Funct,BNLMS, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Jiangxi Normal Univ, Natl Engn Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China
来源：
CHINESE CHEMICAL LETTERS | 2017年 / 28卷 / 08期
基金：
中国国家自然科学基金;
关键词：
Reductive amination; Synthesis; Alkaloids; Glycosidase inhibitors; Polyhydroxylated indolizidines; CASTANOSPERMUM-AUSTRALE; SAKURAI REACTION; D-GULONOLACTONE; AQUEOUS-MEDIA; GLUCOSIDASE-I; DERIVATIVES; INHIBITION; (+)-1-EPI-CASTANOSPERMINE; (+)-CASTANOSPERMINE; 1,6-DIEPICASTANOSPERMINE;
D O I：
10.1016/j.cclet.2017.05.013
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
1-epi-Castanospermine (5) was synthesized from readily available 2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin (11) in 9 steps and 21% overall yield, with selective debenzylation, Barbier reaction and reductive amination as the main reaction steps. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码：1688 / 1692
页数：5
相关论文
共 39 条
[1]   ACARBOSE - AN UPDATE OF ITS PHARMACOLOGY AND THERAPEUTIC USE IN DIABETES-MELLITUS [J].
BALFOUR, JA ;
MCTAVISH, D .
DRUGS, 1993, 46 (06) :1025-1054
[2]   A total synthesis of (+)-negamycin through isoxazolidine allylation [J].
Bates, Roderick W. ;
Khanizeman, Rab'iah Nisha ;
Hirao, Hajime ;
Tay, Yu Shan ;
Sae-Lao, Patcharaporn .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (27) :4879-4884
[3]   TOTAL SYNTHESES OF (+)-CASTANOSPERMINE AND (+)-DEOXYNOJIRIMYCIN [J].
BERNOTAS, RC ;
GANEM, B .
TETRAHEDRON LETTERS, 1984, 25 (02) :165-168
[4]   DIFFERENTIAL INHIBITION BY CASTANOSPERMINE OF VARIOUS INSECT DISACCHARIDASES [J].
CAMPBELL, BC ;
MOLYNEUX, RJ ;
JONES, KC .
JOURNAL OF CHEMICAL ECOLOGY, 1987, 13 (07) :1759-1770
[5]   Novel synthesis of castanospermine and 1-epicastanospermine [J].
Cronin, L ;
Murphy, PV .
ORGANIC LETTERS, 2005, 7 (13) :2691-2693
[6]   Synthesis of (-)-7-epiaustraline and (-)-1-epicastanospermine [J].
Denmark, SE ;
Herbert, B .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :2887-2896
[7]   SYNTHESIS OF THE ENANTIOMERS OF 6-EPICASTANOSPERMINE AND 1,6-DIEPICASTANOSPERMINE FROM D-GULONOLACTONE AND L-GULONOLACTONE [J].
FLEET, GWJ ;
RAMSDEN, NG ;
NASH, RJ ;
FELLOWS, LE ;
JACOB, GS ;
MOLYNEUX, RJ ;
DIBELLO, IC ;
WINCHESTER, B .
CARBOHYDRATE RESEARCH, 1990, 205 :269-282
[8]   INHIBITION OF HIV REPLICATION BY AMINO-SUGAR DERIVATIVES [J].
FLEET, GWJ ;
KARPAS, A ;
DWEK, RA ;
FELLOWS, LE ;
TYMS, AS ;
PETURSSON, S ;
NAMGOONG, SK ;
RAMSDEN, NG ;
SMITH, PW ;
SON, JC ;
WILSON, F ;
WITTY, DR ;
JACOB, GS ;
RADEMACHER, TW .
FEBS LETTERS, 1988, 237 (1-2) :128-132
[9]   SYNTHESIS OF 6-EPICASTANOSPERMINE AND 1,6-DIEPICASTANOSPERMINE FROM L-GULONOLACTONE AND SYNTHESIS OF L-6-EPICASTANOSPERMINE AND L-1,6-DIEPICASTANOSPERMINE FROM D-GULONOLACTONE [J].
FLEET, GWJ ;
RAMSDEN, NG ;
MOLYNEUX, RJ ;
JACOB, GS .
TETRAHEDRON LETTERS, 1988, 29 (29) :3603-3606
[10]   Remote steric effects in the Sakurai reaction [J].
Groaning, MD ;
Meyers, AI .
TETRAHEDRON LETTERS, 1999, 40 (46) :8071-8074
1234