Chemoenzymatic synthesis of enantioenriched 5-oxo-tetrahydro-3-furancarboxylic acid derivatives

被引：26

作者：

Comini, A ^{[1
]}

Forzato, C ^{[1
]}

Nitti, P ^{[1
]}

Pitacco, G ^{[1
]}

Valentin, E ^{[1
]}

机构：

[1] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 04期

关键词：

lactones; enzymatic resolution; baker's yeast; circular dichroism; paraconic acids;

D O I：

10.1016/j.tetasy.2004.01.001

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(R)-(+)-Paraconic acid 4, (S)-(-)-terebic acid 6 and their corresponding methyl and ethyl esters having ee's ranging from 60% to 92% were obtained by enzymatic resolution of their racemates. The enzymatic resolution of racemic ethyl gamma-methylparaconates 14a and 14b allowed the isolation of the unreacted ester (2R,3R)-(+)-14a and that of the lactonic acid (2S,3R)-(-)-5b with 80% and 93% ee, respectively, the former by the use of Horse liver acetone powder (HLAP), the latter using alpha-chymotrypsin (alpha-CT). The enantiomeric ethyl (2S,3S)-(-)-14a and (2S,3R)-(-)-14b, both with >99% ee, were obtained by baker's yeast reduction of diethyl acetylsuccinate. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：617 / 625

页数：9

共 52 条

[11] NOVEL, ENANTIOSELECTIVE LACTONE CONSTRUCTION - 1ST SYNTHESIS OF METHYLENOLACTOCIN, ANTITUMOR ANTIBIOTIC FROM PENICILLIUM SP [J].

DEAZEVEDO, MBM ;

MURTA, MM ;

GREENE, AE .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) :4567-4569

[12] Synthesis of (+)- and (-)-phaseolinic acid by combination of enzymatic hydrolysis and chemical transformations with revision of the absolute configuration of the natural product [J].

Drioli, S ;

Felluga, F ;

Forzato, C ;

Nitti, P ;

Pitacco, G ;

Valentin, E .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2385-2388

[13] A facile route to (+)- and (-)-trans-tetrahydro-5-oxo-2-pentylfuran-3-carboxylic acid, precursors of (+)- and (-)-methylenolactocin [J].

Drioli, S ;

Felluga, F ;

Forzato, C ;

Nitti, P ;

Pitacco, G .

CHEMICAL COMMUNICATIONS, 1996, (11) :1289-1290

[14]

DRIOLI S, 1997, J MOL CATAL B-ENZYM, V3, P2203

[15]

Forzato C, 1999, TARG HETEROCYCL SYST, V3, P93

[16] Baker's yeast reduction of cyclic δ-ketoesters:: synthesis and chiroptical properties of condensed δ-lactones [J].

Forzato, C ;

Nitti, P ;

Pitacco, G ;

Valentin, E .

TETRAHEDRON-ASYMMETRY, 1999, 10 (07) :1243-1254

[17] STUDIES OF GLYCOSIDE OF AUCUBA JAPONICA .19. SEVERAL REACTIONS OF TETRAHYDROANHYDROAUCUBIGENONE [J].

FUJISE, S ;

UDA, H ;

MARUYAMA, M .

NIPPON KAGAKU ZASSHI, 1961, 82 (03) :367-&

[18] RADICAL ADDITIONS OF ALCOHOLS TO ESTERS OF FUMARIC AND MALEIC ACIDS [J].

FUKUNISHI, K ;

INOUE, Y ;

KISHIMOTO, Y ;

MASHIO, F .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (05) :628-632

[19]

GIELEN M, Patent No. 848008

[20] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES [J].

HOFFMANN, HMR ;

RABE, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (02) :94-110

← 1 2 3 4 5 6 →