Template-promoted dimerization of C-allylglycine:: A convenient synthesis of (S,S)-2,7-diaminosuberic acid

被引：40

作者：

O'Leary, DJ

Miller, SJ

Grubbs, RH ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Arnold & Mabel Beckman Lab Chem Synth, Pasadena, CA 91125 USA

[2] Pomona Coll, Dept Chem, Claremont, CA 91711 USA

[3] Boston Coll, Dept Chem, Chestnut Hill, MA 02167 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 13期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(98)00126-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(S,S)-2,7-diaminosuberic acid can be synthesized in a convenient manner using an intramolecular ruthenium-catalyzed ring closing metathesis reaction of BOC-protected C-allylglycine anchored to a catechol template. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1689 / 1690

页数：2

相关论文

共 10 条

[1] KINETIC RESOLUTION OF UNNATURAL AND RARELY OCCURRING AMINO-ACIDS - ENANTIOSELECTIVE HYDROLYSIS OF N-ACYL AMINO-ACIDS CATALYZED BY ACYLASE-I [J].

CHENAULT, HK ;

DAHMER, J ;

WHITESIDES, GM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6354-6364

[2] Synthesis and evaluation of novel substrates and inhibitors of N-Succinyl-LL-diaminopimelate aminotransferase (DAP-AT) from Escherichia coli [J].

Cox, RJ ;

Sherwin, WA ;

Lam, LKP ;

Vederas, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (32) :7449-7460

[3] Single-step synthesis of cell-permeable protein dimerizers that activate signal transduction and gene expression [J].

Diver, ST ;

Schreiber, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (22) :5106-5109

[4] SYNTHESIS OF CYCLOALKENES VIA ALKYLIDENE-MEDIATED OLEFIN METATHESIS AND CARBONYL OLEFINATION [J].

FU, GC ;

GRUBBS, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) :3800-3801

[5] RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS [J].

GRUBBS, RH ;

MILLER, SJ ;

FU, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) :446-452

[6] Application of ring-closing metathesis to the synthesis of rigidified amino acids and peptides [J].

Miller, SJ ;

Blackwell, HE ;

Grubbs, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (40) :9606-9614

[7] Highly practical methodology for the synthesis of D- and L-alpha-amino acids, N-protected alpha-amino acids, and N-methyl-alpha-amino acids [J].

Myers, AG ;

Gleason, JL ;

Yoon, T ;

Kung, DW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (04) :656-673

[8] USEFUL INTERMEDIATES FOR SYNTHESIS OF DICARBA ANALOGS OF CYSTINE PEPTIDES - SELECTIVELY PROTECTED ALPHA-AMINOSUBERIC ACID AND ALPHA-ALPHA'-DIAMINOSUBERIC ACID OF DEFINED STEREOCHEMISTRY [J].

NUTT, RF ;

STRACHAN, RG ;

VEBER, DF ;

HOLLY, FW .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (15) :3078-3080

[9] CATALYTIC RING-CLOSING METATHESIS - A NEW, POWERFUL TECHNIQUE FOR CARBON-CARBON COUPLING IN ORGANIC-SYNTHESIS [J].

SCHMALZ, HG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17) :1833-1836

[10] ASYMMETRIC-SYNTHESIS OF 2,6-DIAMINOPIMELIC ACIDS [J].

WILLIAMS, RM ;

YUAN, CG .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6519-6527