ENANTIOSELECTIVE SYNTHESIS OF LORACARBEF FROM SODIUM ERYTHROBATE

被引：32

作者：

FRAZIER, JW ^{[1
]}

STASZAK, MA ^{[1
]}

WEIGEL, LO ^{[1
]}

机构：

[1] ELI LILLY & CO,LILLY RES LAB,DIV CHEM PROC RES & DEV,INDIANAPOLIS,IN 46285

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(00)91559-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sodium erythorbate (7) has been converted to loracarbef (1). Oxidation of sodium erythorbate to D-erythronolactone (8) followed by selective monotosylation and treatment with sodium ethoxide provided ethyl (2S,3R)-4-hydroxy-2,3-epoxybutyrate (10). Swern oxidation of this epoxide into the aldehyde (11), imine formation with tert-butylglycinate and an enantioselective Staudinger reaction with phthalimidoacetyl chloride afforded the (3S,4S)-cis-beta-lactam (13). Appropriate functional group manipulations followed by a Dieckmann condensation, chlorination, and protecting group removals gave the enantiomerically pure nucleus of loracarbef (24).

引用

页码：857 / 860

页数：4

共 24 条

[1]

AIKINS J, 1991, 201ST NAT M AM CHEM

[2] AN ENANTIOSELECTIVE SYNTHESIS OF LORACARBEF (LY163892/KT3777) [J].

BODUROW, CC ;

BOYER, BD ;

BRENNAN, J ;

BUNNELL, CA ;

BURKS, JE ;

CARR, MA ;

DOECKE, CW ;

ECKRICH, TM ;

FISHER, JW ;

GARDNER, JP ;

GRAVES, BJ ;

HINES, P ;

HOYING, RC ;

JACKSON, BG ;

KINNICK, MD ;

KOCHERT, CD ;

LEWIS, JS ;

LUKE, WD ;

MOORE, LL ;

MORIN, JM ;

NIST, RL ;

PRATHER, DE ;

SPARKS, DL ;

VLADUCHICK, WC .

TETRAHEDRON LETTERS, 1989, 30 (18) :2321-2324

[3]

BOYER BD, 1990, Patent No. 365212

[4]

BRENNAN J, 1990, Patent No. 365213

[5] ENANTIOSPECIFIC SYNTHESES OF LEUKOTRIENE-C4, LEUKOTRIENE-D4, AND LEUKOTRIENE-E4 AND [14,15-H-3(2)]LEUKOTRIENE-E4 DIMETHYL ESTER [J].

COHEN, N ;

BANNER, BL ;

LOPRESTI, RJ ;

WONG, F ;

ROSENBERGER, M ;

LIU, YY ;

THOM, E ;

LIEBMAN, AA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (11) :3661-3672

[6] CHIRAL CONTROL OF THE STAUDINGER REACTION [J].

COOPER, RDG ;

DAUGHERTY, BW ;

BOYD, DB .

PURE AND APPLIED CHEMISTRY, 1987, 59 (03) :485-492

[7] SYNTHESIS OF ALKYL (2S,3R)-4-HYDROXY-2,3-EPOXYBUTYRATES FROM SODIUM ERYTHORBATE [J].

DUNIGAN, J ;

WEIGEL, LO .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6225-6227

[8] THE ASYMMETRIC-SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .5. APPLICATION OF CHIRAL ALPHA,BETA-EPOXYIMINES IN KETENE-IMINE CYCLO-ADDITION REACTIONS LEADING TO HOMOCHIRAL 3-AMINOAZETIDINONES [J].

EVANS, DA ;

WILLIAMS, JM .

TETRAHEDRON LETTERS, 1988, 29 (40) :5065-5068

[9]

EVANS DA, 1985, TETRAHEDRON LETT, V26, P3878

[10] SELECTIVE TRANSFORMATIONS OF THREO-2,3-DIHYDROXY ESTERS [J].

FLEMING, PR ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2869-2875

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