ENANTIOSPECIFIC SYNTHESIS OF R-5,6-DIHYDROXY-2-(N,N-DI-NORMAL-PROPYLAMINO) AND S-5,6-DIHYDROXY-2-(N,N-DI-NORMAL-PROPYLAMINO)TETRALINS FROM SERINE

被引：19

作者：

BAXTER, AD ^{[1
]}

MURRAY, PJ ^{[1
]}

TAYLOR, RJK ^{[1
]}

机构：

[1] UNIV E ANGLIA,SCH CHEM SCI,NORWICH NR4 7TJ,NORFOLK,ENGLAND

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 17期

关键词：

D O I：

10.1016/S0040-4039(00)74203-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

The first enantiospecific synthesis of 5,6-dihydroxy-2-(NN-di-n-propylamino)tetralin [5,6-(HO)2DPAT] is reported. Starting from D- or L-serine either enantiomer is readily available in high optical purity.

引用

页码：2331 / 2334

页数：4

共 12 条

[1]

STEREOSELECTIVE MONO-HOMOLOGATION AND BIS-HOMOLOGATION OF L-SERINAL VIA 2-TRIMETHYLSILYLTHIAZOLE ADDITION - THE THIAZOLE ROUTE TO AMINO L-SUGARS AND D-ERYTHRO-SPHINGOSINES [J].

DONDONI, A ;

FANTIN, G ;

FOGAGNOLO, M ;

MEDICI, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (01) :10-12

[2]

FLUCKIGER E, 1989, BASIC CLIN ASPECTS N, V3

[3]

GLYCOSYL ALPHA-AMINO-ACIDS VIA STEREOCONTROLLED BUILDUP OF A PENALDIC ACID EQUIVALENT - A NOVEL SYNTHETIC APPROACH TO THE NUCLEOSIDIC COMPONENT OF THE POLYOXINS AND RELATED SUBSTANCES [J].

GARNER, P ;

PARK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3772-3787

[4]

STEREOCONTROLLED ADDITION TO A PENALDIC ACID EQUIVALENT - AN ASYMMETRIC-SYNTHESIS OF THREO-BETA-HYDROXY-L-GLUTAMIC ACID [J].

GARNER, P .

TETRAHEDRON LETTERS, 1984, 25 (51) :5855-5858

[5]

THE SYNTHESIS AND CONFIGURATIONAL STABILITY OF DIFFERENTIALLY PROTECTED BETA-HYDROXY-ALPHA-AMINO ALDEHYDES [J].

GARNER, P ;

PARK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2361-2364

[6]

RESOLUTION OF 5,6-DIHYDROXY-2-(N,N-DI-NORMAL-PROPYLAMINO)TETRALIN IN RELATION TO THE STRUCTURAL AND STEREOCHEMICAL REQUIREMENTS FOR CENTRALLY ACTING DOPAMINE AGONISTS [J].

GROL, CJ ;

JANSEN, LJ ;

ROLLEMA, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (05) :679-683

[7]

SYNTHESIS OF D-ERYTHRO-SPHINGOSINE AND D-THREO-SPHINGOSINE DERIVATIVES FROM L-SERINE [J].

HEROLD, P .

HELVETICA CHIMICA ACTA, 1988, 71 (02) :354-362

[8]

SYNTHESIS AND PHARMACOLOGY OF SOME 2-AMINOTETRALINS - DOPAMINE RECEPTOR AGONISTS [J].

MCDERMED, JD ;

MCKENZIE, GM ;

PHILLIPS, AP .

JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (04) :362-367

[9]

PRACTICAL ENANTIOSELECTIVE SYNTHESIS OF A HOMOTYROSINE DERIVATIVE AND (R,R)-4-PROPYL-9-HYDROXYNAPHTHOXAZINE, A POTENT DOPAMINE AGONIST [J].

MELILLO, DG ;

LARSEN, RD ;

MATHRE, DJ ;

SHUKIS, WF ;

WOOD, AW ;

COLLELUORI, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (23) :5143-5150

[10]

A STRAIGHTFORWARD SYNTHESIS OF ALLYL AMINES FROM ALPHA-AMINO-ACIDS WITHOUT RACEMIZATION [J].

MORIWAKE, T ;

HAMANO, S ;

SAITO, S ;

TORII, S .

CHEMISTRY LETTERS, 1987, (10) :2085-2088

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