STEREOCONTROLLED SYNTHESIS OF BETA-HYDROXYPHENYLALANINE AND BETA-HYDROXYTYROSINE DERIVATIVES

被引：48

作者：

EASTON, CJ

HUTTON, CA

ROSELT, PD

TIEKINK, ERT

机构：

[1] Department of Chemistry, University of Adelaide, Adelaide

来源：

TETRAHEDRON | 1994年 / 50卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(01)85256-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Side-chain bromination of N-phthaloyl-(S)-phenylalanine and tyrosine derivatives, followed by treatment of the product bromides with silver nitrate in aqueous acetone, affords the corresponding (2S,3R)-beta-hydroxy-alpha-amino acids, enantiospecifically and diastereoselectively. The diastereoselectivity depends on the carboxyl protecting group, tert-Butyl esters display greater stereoselectivity than the corresponding methyl esters, presumably as a result of a steric effect, while N-tert-butylamides react diastereospecifically due to a combination of steric and electronic effects.

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收藏

页码：7327 / 7340

页数：14

相关论文

共 57 条

[1] USE OF ETHOXYACETYLENE FOR SYNTHESIS OF N-PROTECTED AMINO-ACIDS [J].

BANKS, GR ;

COHEN, D ;

PATTENDE.GE ;

THOMAS, JAG .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (02) :126-&

[2] GENERAL-METHOD OF DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF BETA-HYDROXY-ALPHA-AMINO ACIDS BY CONDENSATION OF ALDEHYDES AND KETONES WITH GLYCINE [J].

BELOKON, YN ;

BULYCHEV, AG ;

VITT, SV ;

STRUCHKOV, YT ;

BATSANOV, AS ;

TIMOFEEVA, TV ;

TSYRYAPKIN, VA ;

RYZHOV, MG ;

LYSOVA, LA ;

BAKHMUTOV, VI ;

BELIKOV, VM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (14) :4252-4259

[3] RESEARCHES ON ACETYLENIC COMPOUNDS .1. THE PREPARATION OF ACETYLENIC KETONES BY OXIDATION OF ACETYLENIC CARBINOLS AND GLYCOLS [J].

BOWDEN, K ;

HEILBRON, IM ;

JONES, ERH ;

WEEDON, BCL .

JOURNAL OF THE CHEMICAL SOCIETY, 1946, (JAN) :39-45

[4] METAL-DIRECTED ASYMMETRIC-SYNTHESIS OF DIASTEREOISOMERIC BETA-PHENYL SERINES USING (+)-KETOPINIC ACID AS A CHIRAL AUXILIARY [J].

CASELLA, L ;

JOMMI, G ;

MONTANARI, S ;

SISTI, M .

TETRAHEDRON LETTERS, 1988, 29 (17) :2067-2068

[5] N-PHTHALOYLATION OF CHLORO-2-AMINO-ACIDS AND HYDROXY-2-AMINO-ACIDS [J].

CLARKE, S ;

HIDER, RC ;

JOHN, DI .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (03) :230-234

[6] STRUCTURE ELUCIDATION OF PHOMOPSIN-A, A NOVEL CYCLIC HEXAPEPTIDE MYCO-TOXIN PRODUCED BY PHOMOPSIS-LEPTOSTROMIFORMIS [J].

CULVENOR, CCJ ;

COCKRUM, PA ;

EDGAR, JA ;

FRAHN, JL ;

GORSTALLMAN, CP ;

JONES, AJ ;

MARASAS, WFO ;

MURRAY, KE ;

SMITH, LW ;

STEYN, PS ;

VLEGGAAR, R ;

WESSELS, PL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (21) :1259-1262

[7] SPECIFIC-INHIBITION OF HUMAN BETA-D-GLUCURONIDASE AND ALPHA-L-IDURONIDASE BY A TRIHYDROXY PIPECOLIC ACID OF PLANT-ORIGIN [J].

DIBELLO, IC ;

DORLING, P ;

FELLOWS, L ;

WINCHESTER, B .

FEBS LETTERS, 1984, 176 (01) :61-64

[8] SYNTHESIS OF HOMOCHIRAL HYDROXY-ALPHA-AMINO ACID-DERIVATIVES [J].

EASTON, CJ ;

HUTTON, CA ;

TAN, EW ;

TIEKINK, ERT .

TETRAHEDRON LETTERS, 1990, 31 (48) :7059-7062

[9] BROMINATION OF N-PHTHALOYLAMINO ACID-DERIVATIVES [J].

EASTON, CJ ;

TAN, EW ;

HAY, MP .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (07) :385-386

[10] REGIOSELECTIVE FUNCTIONALIZATION OF N-PHTHALOYL-SUBSTITUTED AMINO-ACID AND PEPTIDE DERIVATIVES [J].

EASTON, CJ ;

HUTTON, CA ;

ROSITANO, G ;

TAN, EW .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5614-5618

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