APPLICATIONS OF CROTYLDIISOPINOCAMPHEYLBORANES IN SYNTHESIS - THE TOTAL SYNTHESIS OF NIKKOMYCIN-B

被引：66

作者：

BARRETT, AGM ^{[1
]}

LEBOLD, SA ^{[1
]}

机构：

[1] NORTHWESTERN UNIV,DEPT CHEM,EVANSTON,IL 60208

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 16期

关键词：

D O I：

10.1021/jo00016a014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(-)-(E)-Crotyldiisopinocampheylborane was employed in a highly diastereoselective and enantioselective synthesis of the gamma-hydroxy-beta-methyl-alpha-aminobutanoic acid moiety of nikkomycin B. A protected derivative of this N-terminal amino acid residue was condensed with uracil polyoxin C benzyl ester to provide, on deprotection, the antifungal agent nikkomycin B.

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页码：4875 / 4884

页数：10

相关论文

共 57 条

[1] AMINO-ACIDS AND PEPTIDES .2. NEW METHOD FOR PREPARING DIAZODIPHENYLMETHANE AND RELATED COMPOUNDS [J].

ADAMSON, JR ;

BYWOOD, R ;

EASTLICK, DT ;

GALLAGHER, G ;

WALKER, D ;

WILSON, EM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (20) :2030-2033

[2] TOTAL, ASYMMETRIC-SYNTHESIS OF DEOXYPOLYOXIN-C [J].

AUBERSON, Y ;

VOGEL, P .

TETRAHEDRON, 1990, 46 (20) :7019-7032

[3]

AZUMA T, 1977, CHEM PHARM BULL, V25, P1740

[4] ALPHA-METHOXYVINYLLITHIUM AND RELATED METALATED ENOL ETHERS - PRACTICAL REAGENTS FOR NUCLEOPHILIC ACYLATION [J].

BALDWIN, JE ;

HOFLE, GA ;

LEVER, OW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (22) :7125-7127

[5] NOVEL ANIONIC REAGENTS FOR THE STEREOSELECTIVE SYNTHESIS OF GAMMA-HYDROXY-ALPHA-AMINO-ACIDS - AN X-RAY CRYSTALLOGRAPHIC STUDY OF 2R(S)-BENZOYLAMINO-N-TERT-BUTYL-4R(S)-HYDROXY-4-(4-METHOXYPHENYL)-3R(S)-METHYLBUTANAMIDE [J].

BANKS, BJ ;

BARRETT, AGM ;

RUSSELL, MA ;

WILLIAMS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (16) :873-875

[6] APPLICATION OF (CHLOROMETHYL)ALUMINUM 2-(2-PROPENYL)ANILIDE IN THE CONVERSION OF GAMMA-LACTONE AND DELTA-LACTONE INTO PROTECTED HYDROXY-ACIDS [J].

BARRETT, AGM ;

BEZUIDENHOUDT, BCB ;

DHANAK, D ;

GASIECKI, AF ;

HOWELL, AR ;

LEE, AC ;

RUSSELL, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (14) :3321-3324

[7] 3-BUTENYL ESTERS AS CONVENIENT PROTECTING GROUPS FOR CARBOXYLIC-ACIDS [J].

BARRETT, AGM ;

LEBOLD, SA ;

ZHANG, XA .

TETRAHEDRON LETTERS, 1989, 30 (52) :7317-7320

[8] ALPHA-OXIMINO AMIDE TRIANIONS IN THE STEREOSELECTIVE SYNTHESIS OF ISOXAZOLINES AND GAMMA-HYDROXY-ALPHA-AMINO ACIDS [J].

BARRETT, AGM ;

DHANAK, D ;

LEBOLD, SA ;

RUSSELL, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1894-1901

[9] (PHENYLTHIO)NITROMETHANE IN THE TOTAL SYNTHESIS OF POLYOXIN-C [J].

BARRETT, AGM ;

LEBOLD, SA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3853-3857

[10] THE TOTAL SYNTHESIS OF NIKKOMYCIN-B [J].

BARRETT, AGM ;

LEBOLD, SA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5818-5820

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