THE ENANTIOSELECTIVE SYNTHESIS OF SIMPLIFIED SOUTHERN-HALF FRAGMENTS OF SORAPHEN-A

被引：33

作者：

LOUBINOUX, B

SINNES, JL

OSULLIVAN, AC

WINKLER, T

机构：

[1] FAC SCI VANDOEUVRE NANCY,CHIM ORGAN LAB 4,F-54506 VANDOEUVRE NANCY,FRANCE

[2] CIBA GEIGY AG,DIV PLANT PROTECT,CH-4002 BASEL,SWITZERLAND

来源：

TETRAHEDRON | 1995年 / 51卷 / 12期

关键词：

D O I：

10.1016/0040-4020(95)00098-S

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The compound 2 comprises a southern-half subunit of the fungicidal macrolide soraphen A 1. It was prepared by a Meinwald reaction of the enolate of S-7 with the lactone S-8. Its enantiomer and diastereomers were synthesized in a similar manner. The lactone S-8 and its enantiomer R-8 were prepared by three different routes, including the enantioselective catalytic reduction of the beta-keto ester 17. These lactones are new and potentially useful as C-5 asymmetric building blocks.

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页码：3549 / 3558

页数：10

相关论文

共 46 条

[1]

ABEL S, 1994, ANGEW CHEM, P2522

[2] FLUOROOLEFIN DIPEPTIDE ISOSTERES .1. THE SYNTHESIS OF GLY-PSI(CF=CH)GLY AND RACEMIC PHE-PSI(CF=CH)GLY [J].

ALLMENDINGER, T ;

FURET, P ;

HUNGERBUHLER, E .

TETRAHEDRON LETTERS, 1990, 31 (50) :7297-7300

[3]

BEDORF N, 1993, LIEBIGS ANN CHEM, P1017

[4]

Braun M., 1992, ADV CARBANION CHEM, V1, P177

[5] SUBSTRATE MODIFICATION AS A MEANS OF ENHANCING THE ENANTIOSELECTIVITY OF MICROBIAL REDUCTIONS OF BETA-KETO-ESTERS - AN (R)-1,3,5-TRIHYDROXYPENTANE OR (S)-1,3,5-TRIHYDROXYPENTANE SYNTHON [J].

BROOKS, DW ;

KELLOGG, RP ;

COOPER, CS .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :192-196

[6] SYNTHESIS OF 1,5-BIFUNCTIONALIZED OPTICALLY-ACTIVE 3-PENTANOL AS A REVERSIBLE CHIRAL BUILDING BLOCK - ASYMMETRIC REDUCTION OF 4-(1,3-DITHIAN-2-YL)-3-OXOBUTANOATES WITH FERMENTING BAKERS-YEAST [J].

CHIKASHITA, H ;

OHKAWA, K ;

ITOH, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (11) :3513-3517

[7] SYNTHETIC STUDIES ON 2R,4',8'R-ALPHA-TOCOPHEROL - APPROACH UTILIZING SIDE-CHAIN SYNTHONS OF MICROBIOLOGICAL ORIGIN [J].

COHEN, N ;

EICHEL, WF ;

LOPRESTI, RJ ;

NEUKOM, C ;

SAUCY, G .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (22) :3505-3511

[8] REQUIREMENTS FOR STEREOSPECIFICITY IN HYDROLYSIS BY ALPHA-CHYMOTRYPSIN .4. HYDROXYL SUBSTITUENT - ABSOLUTE CONFIGURATIONS [J].

COHEN, SG ;

KHEDOURI, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (20) :4228-&

[9]

DUGGAN AJ, 1978, TETRAHEDRON LETT, V45, P4323

[10] TOTAL SYNTHESIS OF (+)-A83543A [(+)-LEPICIDIN-A] [J].

EVANS, DA ;

BLACK, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) :4497-4513

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