Efficient synthesis of 3-hydroxyprolines and 3-hydroxyprolinols from sugars

被引：25

作者：

Lee, JH ^{[1
]}

Kang, JE ^{[1
]}

Yang, MS ^{[1
]}

Kang, KY ^{[1
]}

Park, KH ^{[1
]}

机构：

[1] Gyeongsang Natl Univ, Dept Agr Chem, Div Appl Life Sci, Chinju 660701, South Korea

来源：

TETRAHEDRON | 2001年 / 57卷 / 51期

关键词：

trans-3-hydroxy-L-proline; trans-3-hydroxyl-prolinol; cis-3-hydroxy-D-proline; cis-3-hydroxy-D-prolinol;

D O I：

10.1016/S0040-4020(01)01070-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trans-3-Hydroxy-L- proline 1, trans-3-hydroxy-L-prolinol 2. cis-3-hydroxy-D-prolinol 3, and cis-3-hydroxy-D-prolinol 4 have been prepared in enantiomerically pure form with chirospecific manner. Key intermediates, 2-amino-3-hydroxy-4-pentenoate 9 and 17, were obtained from D-glucono-delta -lactone and L-gulonic acid gamma -lactone via a simultaneous dealkoxyhalogenation. (C) 2001 Elsevier Science Ltd. All rights reserved,

引用

页码：10071 / 10076

页数：6

共 20 条

[1] BAKERS-YEAST REDUCTIONS OF BETA-OXOPYRROLIDINECARBOXYLATES - SYNTHESIS OF (+)-CIS-(2R,3S)-3-HYDROXYPROLINE AND (-)-(1S,5S)-GEISSMAN-WAISS LACTONE, A USEFUL PRECURSOR TO PYRROLIZIDINE ALKALOIDS
COOPER, J
GALLAGHER, PT
KNIGHT, DW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (12): : 1313 - 1317
[2] A straightforward synthesis of (2S,3R)-3-hydroxyproline and trans-(2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidine
DellUomo, N
DiGiovanni, MC
Misiti, D
Zappia, G
DelleMonache, G
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (01) : 181 - 188
[3] Reductive cyanation:: A key step for a short synthesis of (-)-(2S,3S)-3-hydroxyproline
Durand, JO
Larchevêque, M
Petit, Y
[J]. TETRAHEDRON LETTERS, 1998, 39 (32) : 5743 - 5746
[4] 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]
FLEET, GWJ
WITTY, DR
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (02) : 119 - 136
[5] POLYHYDROXYLATED PYRROLIDINES FROM SUGAR LACTONES - SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO-D-GLUCITOL FROM D-GALACTONOLACTONE AND SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-ALLITOL, 1,4-DIDEOXY-1,4-IMINO-D-RIBITOL, AND (2S,3R,4S)-3,4-DIHYDROXYPROLINE FROM D-GULONOLACTONE
FLEET, GWJ
SON, JC
[J]. TETRAHEDRON, 1988, 44 (09) : 2637 - 2647
[6] CHIRAL POOL SYNTHESIS OF TRANS-(2S,3S)-3-HYDROXYPROLINE AND CASTANODIOL FROM S-PYROGLUTAMIC ACID
HERDEIS, C
HUBMANN, HP
LOTTER, H
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (01) : 119 - 128
[7] HIGHLY STEREOSELECTIVE SYNTHESIS OF CIS-(2R,3S)-3-HYDROXYPROLINE
JURCZAK, J
PROKOPOWICZ, P
GOLEBIOWSKI, A
[J]. TETRAHEDRON LETTERS, 1993, 34 (44) : 7107 - 7110
[8] Chirospecific synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol and 1,4-dideoxy-1,4-imino-L-xylitol via one-pot cyclisation
Kim, JH
Yang, MS
Lee, WS
Park, KH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (17): : 2877 - 2880
[9] A synthesis of the derivatives of 1,2,3,5,10,10a-hexahydrobenz[f]indolizine-6,9-dione having antifungal activity as a simple model of saframycin A
Kubo, A
Nakai, T
Koizumi, Y
Kitahara, Y
Saito, N
Mikami, Y
Yazawa, K
Uno, J
[J]. HETEROCYCLES, 1996, 42 (01) : 195 - 211
[10] Lee BW, 2000, SYNTHESIS-STUTTGART, P1305

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