Chemoenzymatic synthesis of both enantiomers of cis-6-(hydroxymethyl)- and cis,cis-4-hydroxy-6-(hydroxymethyl)pipecolic acids

被引：12

作者：

Chênevert, R ^{[1
]}

Morin, MP ^{[1
]}

机构：

[1] Univ Laval, Fac Sci & Genie, Dept Chim, Quebec City, PQ G1K 7P4, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 09期

关键词：

D O I：

10.1021/jo9823036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both enantiomers of cis-6-(hydroxymethyl)- and cis, cis-4-hydroxy-6-(hydroxymethyl)pipecolic acids, piperidine-based nonproteinogenic amino acids, have been synthesized from starting materials obtained from enzymatic desymmetrizations.

引用

页码：3178 / 3180

页数：3

共 23 条

[1] Asymmetric routes to substituted piperidines [J].

Bailey, PD ;

Millwood, PA ;

Smith, PD .

CHEMICAL COMMUNICATIONS, 1998, (06) :633-640

[2] Enantioselective synthesis of substituted pipecolic acid derivatives [J].

Barluenga, J ;

Aznar, F ;

Valdés, C ;

Ribas, C .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) :3918-3924

[3]

BARRETT GC, 1985, CHEM BIOCH AMINO ACI

[4] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[5] Chemoenzymatic synthesis of both enantiomers of cis-6-hydroxymethylpipecolic acid [J].

Chenevert, R ;

Morin, MP .

TETRAHEDRON-ASYMMETRY, 1996, 7 (08) :2161-2164

[6] Enzymatic route to chiral, nonracemic cis-2,6- and cis,cis-2,4,6-substituted piperidines. Synthesis of (+)-dihydropinidine and dendrobate alkaloid (+)-241D [J].

Chenevert, R ;

Dickman, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3332-3341

[7] PROBING PROTEIN-STRUCTURE AND FUNCTION WITH AN EXPANDED GENETIC-CODE [J].

CORNISH, VW ;

MENDEL, D ;

SCHULTZ, PG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (06) :621-633

[8] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

DUTHALER, RO .

TETRAHEDRON, 1994, 50 (06) :1539-1650

[9] Small ring constrained peptidomimetics.: Synthesis of aziridine parallel β-sheet mimetics [J].

Filigheddu, SN ;

Taddei, M .

TETRAHEDRON LETTERS, 1998, 39 (22) :3857-3860

[10]

GANTE J, 1994, ANGEW CHEM INT EDIT, V33, P1699, DOI 10.1002/anie.199416991

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