Total synthesis of 1-deoxygulonojirimycin. Revision of the absolute configuration of the natural product

被引：27
作者：
Pyun, SJ
Lee, KY
Oh, CY
Joo, JE
Cheon, SH
Ham, WH [1 ]
机构：
[1] Sungkyunkwan Univ, Coll Pharm, Suwon 440746, South Korea
[2] Chonnam Natl Univ, Coll Pharm, Kwangju 500757, South Korea
来源：
TETRAHEDRON | 2005年 / 61卷 / 06期
关键词：
polyhydroxylated piperidines; azasugars; synthesis; oxazoline;
D O I：
10.1016/j.tet.2004.12.001
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A concise. stereoselective synthesis of 1-deoxygulonojirimycin was achieved and the absolute configuration of the natural product was revised. Key features involve diastereoselective oxazoline formation catalyzed by palladium(0). ROM-and dihydroxylation. (C) 2004 Elsevier Ltd. All rights reserved.
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收藏
页码：1413 / 1416
页数：4
相关论文
共 55 条
[1]   Enantioselective synthesis of 1-deoxy-D-gulonojirimycin from a phenylglycinol-derived lactam [J].
Amat, M ;
Huguet, M ;
Llor, N ;
Bassas, O ;
Gómez, AM ;
Bosch, J ;
Badia, J ;
Baldoma, L ;
Aguilar, J .
TETRAHEDRON LETTERS, 2004, 45 (28) :5355-5358
[2]   In vitro inhibition and intracellular enhancement of lysosomal α-galactosidase A activity in Fabry lymphoblasts by 1-deoxygalactonojirimycin and its derivatives [J].
Asano, N ;
Ishii, S ;
Kizu, H ;
Ikeda, K ;
Yasuda, K ;
Kato, A ;
Martin, OR ;
Fan, JQ .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 2000, 267 (13) :4179-4186
[3]   Glycosidase inhibitors: update and perspectives on practical use [J].
Asano, N .
GLYCOBIOLOGY, 2003, 13 (10) :93R-104R
[4]   Novel α-L-fucosidase inhibitors from the bark of Angylocalyx pynaertii (Leguminosae) [J].
Asano, N ;
Yasuda, K ;
Kizu, H ;
Kato, A ;
Fan, JQ ;
Nash, RJ ;
Fleet, GWJ ;
Molyneux, RJ .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 2001, 268 (01) :35-41
[5]   ACYCLIC STEREOCONTROL INDUCED BY ALLYLIC ALKOXY GROUPS - SYNTHETIC APPLICATIONS OF STEREOSELECTIVE DIHYDROXYLATION IN NATURAL PRODUCT SYNTHESIS [J].
CHA, JK ;
KIM, NS .
CHEMICAL REVIEWS, 1995, 95 (06) :1761-1795
[6]   ON STEREOCHEMISTRY OF OSMIUM-TETROXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].
CHA, JK ;
CHRIST, WJ ;
KISHI, Y .
TETRAHEDRON LETTERS, 1983, 24 (37) :3943-3946
[7]   Total synthesis of (-)- and (+)-lentiginosine [J].
Chandra, KL ;
Chandrasekhar, M ;
Singh, VK .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4630-4633
[8]   Stereoselective synthesis of MeBmt and methyl (4R,5S)-5-isopropyl-2-phenyloxazoline-4-carboxylate by a Pd-catalyzed equilibration [J].
Cook, GR ;
Shanker, PS .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6818-6822
[9]   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
[10]   Inhibitors of carbohydrate-processing enzymes: Design and synthesis of sugar-shaped heterocycles [J].
Ganem, B .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (07) :340-347
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