A SHORT DIASTEREOSELECTIVE SYNTHESIS OF THE NATURAL (2R, 3R, 4R)-2-HYDROXYMETHYL-3,4-DIHYDROXYPYRROLIDINE

被引：29

作者：

GRIFFARTBRUNET, D ^{[1
]}

LANGLOIS, N ^{[1
]}

机构：

[1] CNRS,INST CHIM SUBST NAT,F-91190 GIF SUR YVETTE,FRANCE

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(00)76651-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,4-Dideoxy-1,4-imino-D-arabinitol 1, a glycosidase inhibitor constituent of Arachniodes standishii(1) and Angylocalyx boutiqueanus(2) was synthesized from (S)-pyroglutamic acid through regioselective ring opening of the epoxide 3.

引用

页码：2889 / 2890

页数：2

共 21 条

[1] SYNTHESIS FROM D-LYXONOLACTONE OF 1,4-DIDEOXY-1,4-IMINO-L-ARABINITOL, A GLUCOSIDASE INHIBITOR WITH INVITRO ANTIVIRAL ACTIVITY [J].

BEHLING, JR ;

CAMPBELL, AL ;

BABIAK, KA ;

NG, JS ;

MEDICH, J ;

FARID, P ;

FLEET, GWJ .

TETRAHEDRON, 1993, 49 (16) :3359-3366

[2] SYNTHESIS OF HOMOCHIRAL BETA-HYDROXY-ALPHA-AMINO-ACIDS [(2S,3R,4R)-3,4-DIHYDROXYPROLINE AND (2S,3R,4R)-3,4-DIHYDROXYPIPECOLIC ACID] AND OF 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL [DAB1] AND FAGOMINE [1,5-IMINO-1,2,5-TRIDEOXY-D-ARABINO-HEXITOL] [J].

FLEET, GWJ ;

WITTY, DR .

TETRAHEDRON-ASYMMETRY, 1990, 1 (02) :119-136

[3] THE SYNTHESIS FROM D-XYLOSE OF THE POTENT AND SPECIFIC ENANTIOMERIC GLUCOSIDASE INHIBITORS, 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL AND 1,4-DIDEOXY-1,4-IMINO-L-ARABINITOL [J].

FLEET, GWJ ;

SMITH, PW .

TETRAHEDRON, 1986, 42 (20) :5685-5692

[4] 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

[5] POTENT COMPETITIVE-INHIBITION OF ALPHA-GALACTOSIDASE AND ALPHA-GLUCOSIDASE ACTIVITY BY 1,4-DIDEOXY-1,4-IMINOPENTITOLS - SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL AND OF BOTH ENANTIOMERS OF 1,4-DIDEOXY-1,4-IMINOARABINITOL [J].

FLEET, GWJ ;

NICHOLAS, SJ ;

SMITH, PW ;

EVANS, SV ;

FELLOWS, LE ;

NASH, RJ .

TETRAHEDRON LETTERS, 1985, 26 (26) :3127-3130

[6] 3,4-DIHYDROXY-2-HYDROXYMETHYLPYRROLIDINE FROM ARACHNIODES-STANDISHII [J].

FURUKAWA, J ;

OKUDA, S ;

SAITO, K ;

HATANAKA, SI .

PHYTOCHEMISTRY, 1985, 24 (03) :593-594

[7] A CONCISE DIASTEREOSELECTIVE SYNTHESIS OF THE NATURAL (2R,3S)-2-HYDROXYMETHYL-3-HYDROXY-PYRROLIDINE [J].

GRIFFARTBRUNET, D ;

LANGLOIS, N .

TETRAHEDRON LETTERS, 1994, 35 (01) :119-122

[8] CHIRAL POOL SYNTHESIS OF TRANS-(2S,3S)-3-HYDROXYPROLINE AND CASTANODIOL FROM S-PYROGLUTAMIC ACID [J].

HERDEIS, C ;

HUBMANN, HP ;

LOTTER, H .

TETRAHEDRON-ASYMMETRY, 1994, 5 (01) :119-128

[9] ALPHA-AMINO ALDEHYDE EQUIVALENTS AS SUBSTRATES FOR RABBIT MUSCLE ALDOLASE - SYNTHESIS OF 1,4-DIDEOXY-D-ARABINITOL AND 2(R),5(R)-BIS(HYDROXYMETHYL)-3(R),4(R)-DIHYDROXYPYRROLIDINE [J].

HUNG, RR ;

STRAUB, JA ;

WHITESIDES, GM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3849-3855

[10]

IKOTA N, 1987, CHEM PHARM BULL, V35, P2140

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