AN EXPEDITIOUS ASYMMETRIC-SYNTHESIS OF ALLOPHENYLNORSTATINE

被引：63

作者：

BUNNAGE, ME

DAVIES, SG

GOODWIN, CJ

ICHIHARA, O

机构：

[1] DYSON PERRINS LAB, S PARKS RD, OXFORD OX1 3QY, ENGLAND

[2] FISONS PLC, DIV PHARMACEUT, RES & DEV LABS, LOUGHBOROUGH LE11 0RH, ENGLAND

来源：

TETRAHEDRON | 1994年 / 50卷 / 13期

关键词：

D O I：

10.1016/S0040-4020(01)89672-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allophenylnorstatine [APNS; (2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid], a novel amino acid found in the kynostatin class of HIV-1 protease inhibitors, has been prepared in 39% overall yield via a tandem conjugate addition-electrophilic hydroxylation protocol using lithium (S)-(alpha-methylbenzyl)benzylamide and (+)-(camphorsulfonyl)oxaziridine. An unprecedented level of molecular recognition between a homochiral beta-amino enolate and a homochiral oxaziridine is identified and the importance of enolate geometry upon hydroxylation stereoselectivity is also addressed.

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收藏

页码：3975 / 3986

页数：12

相关论文

共 21 条

[1] METAL-AMIDES IN ORGANIC-SYNTHESIS .7. STEREODIVERGENT SYNTHESIS OF THE ENOLATES OF A BETA-AMINO ESTER BY USING LITHIUM N-BENZYLTRIMETHYLSILYLAMIDE [J].

ASAO, N ;

UYEHARA, T ;

YAMAMOTO, Y .

TETRAHEDRON, 1990, 46 (13-14) :4563-4572

[2] ASYMMETRIC MICHAEL ADDITIONS OF HOMOCHIRAL MAGNESIUM AMIDES [J].

BUNNAGE, ME ;

DAVIES, SG ;

GOODWIN, CJ ;

WALTERS, IAS .

TETRAHEDRON-ASYMMETRY, 1994, 5 (01) :35-36

[3]

BUNNAGE ME, 1993, SYNLETT, P731

[4] ASYMMETRIC-SYNTHESIS OF HOMOCHIRAL SYN-3-PHENYLISOSERINE AND ANTI-3-PHENYLISOSERINE DERIVATIVES - A PRACTICAL STRATEGY FOR THE SYNTHESIS OF THE TAXOL C-13 SIDE-CHAIN [J].

BUNNAGE, ME ;

DAVIES, SG ;

GOODWIN, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (13) :1375-1376

[5]

BUNNAGE ME, UNPUB

[6] ASYMMETRIC SYNTHESES OF BETA-PHENYLALANINE, ALPHA-METHYL-BETA-PHENYLALANINES AND DERIVATIVES [J].

DAVIES, SG ;

GARRIDO, NM ;

ICHIHARA, O ;

WALTERS, IAS .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (14) :1153-1155

[7] ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS [J].

DAVIES, SG ;

ICHIHARA, O .

TETRAHEDRON-ASYMMETRY, 1991, 2 (03) :183-186

[8] ASYMMETRIC-SYNTHESIS OF SULFINIMINES - APPLICATIONS TO THE SYNTHESIS OF NONRACEMIC BETA-AMINO-ACIDS AND ALPHA-HYDROXYL-BETA-AMINO-ACIDS [J].

DAVIS, FA ;

REDDY, RT ;

REDDY, RE .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6387-6389

[9] ASYMMETRIC HYDROXYLATION OF ENOLATES WITH N-SULFONYLOXAZIRIDINES [J].

DAVIS, FA ;

CHEN, BC .

CHEMICAL REVIEWS, 1992, 92 (05) :919-934

[10] NUCLEAR MAGNETIC-RESONANCE STUDY OF STEREOISOMERIC 2-OXAZOLIDONE AND 2-PHENYL-2-OXAZOLINE DERIVATIVES OF ALPHA-AMINO-BETA-HYDROXY ACIDS [J].

FUTAGAWA, S ;

INUI, T ;

SHIBA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1973, 46 (10) :3308-3310