ASYMMETRIC-SYNTHESIS BY THE CN(R,S) METHOD .27. 1ST ASYMMETRIC-SYNTHESIS OF CARNOSADINE

被引：26

作者：

AITKEN, DJ ^{[1
]}

GUILLAUME, D ^{[1
]}

HUSSON, HP ^{[1
]}

机构：

[1] FAC SCI PHARMACEUT & BIOL PARIS,CHIM THERAPEUT LAB,CNRS,URA 1310,4 AVE OBSERV,F-75270 PARIS 06,FRANCE

来源：

TETRAHEDRON | 1993年 / 49卷 / 29期

关键词：

D O I：

10.1016/S0040-4020(01)80152-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first asymmetric synthesis of the naturally-occurring cyclopropane amino acid carnosadine, 1, has been carried out. Starting from the previously available chiral intermedia 2, appropriate amine protection and side-chain modifications permitted introduction of the key guanidyl substituent in a short and efficient synthesis to give the title compound in five steps and 45% overall yield.

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页码：6375 / 6380

页数：6

相关论文

共 32 条

[1] *REACTIONS COLOREES SPECIFIQUES DE LARGININE ET DE LA TYROSINE REALISEES APRES CHROMATOGRAPHIE SUR PAPIER [J].

ACHER, R ;

CROCKER, C .

BIOCHIMICA ET BIOPHYSICA ACTA, 1952, 9 (06) :704-705

[2] INHIBITION OF PIG-KIDNEY L-AROMATIC AMINO-ACID DECARBOXYLASE BY 2,3-METHANO-META-TYROSINES [J].

AHMAD, S ;

PHILLIPS, RS ;

STAMMER, CH .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (08) :1410-1417

[3] ASYMMETRIC-SYNTHESIS BY THE CN(R,S) METHOD .19. ASYMMETRIC-SYNTHESIS OF 2,3-METHANOHOMOSERINE - A GENERAL-APPROACH TO CHIRAL 2-SUBSTITUTED CYCLOPROPANE AMINO-ACIDS [J].

AITKEN, DJ ;

ROYER, J ;

HUSSON, HP .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2814-2820

[4]

ALAMI A, 1993, B SOC CHIM FR, V130, P5

[5] GUANIDINE COMPOUNDS .2. PREPARATION OF MONO-ALKYLGUANIDINES AND N,N-DI-ALKYLGUANIDINES [J].

BANNARD, RAB ;

CASSELMAN, AA ;

COCKBURN, WF ;

BROWN, GM .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1958, 36 (11) :1541-1549

[6]

BORNSTEIN J, 1963, ORG SYNTH, V4, P810

[7] I-AMINOCYCLOPROPANE-I-CARBOXYLIC ACID - NEW AMINO-ACID IN PERRY PEARS AND CIDER APPLES [J].

BURROUGHS, LF .

NATURE, 1957, 179 (4555) :360-361

[8]

GUILLAUME D, 1991, SYNLETT, P747

[9]

HEBRARD P, 1970, B SOC CHIM FR, P1938

[10] STRUCTURE OF CORONATINE [J].

ICHIHARA, A ;

SHIRAISHI, K ;

SATO, H ;

SAKAMURA, S ;

NISHIYAMA, K ;

SAKAI, R ;

FURUSAKI, A ;

MATSUMOTO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (02) :636-637

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