CHEMICAL SYNTHESIS OF THE (1R,2S) AND (1S,2R) ARENE OXIDE METABOLITES OF ACRIDINE

被引：4

作者：

BOYD, DR

DORRITY, MRJ

HAMILTON, L

MALONE, JF

SMITH, A

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 19期

关键词：

D O I：

10.1039/p19940002711

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiopure samples of (+)-(1R,2S) and (-)-(1S,2R)-1,2-epoxy-1,2-dihydroacridine 4 have been obtained from the corresponding trans-2-bromo-1,2,3,4-tetrahydroacridin-1-ol MTPA esters 7a and b. Absolute configurations were deduced by stereochemical correlation to (+)-(1R,2R)-trans-2-bromo-1-(2-methoxy-2-phenyl-2-trifluoroacetoxy)-1,2,3,4-acridine 7a which was unequivocally assigned by X-ray crystal structure analysis. (-)-(1R,2R)-trans-1,2-Dihydroacridine-1,2-diol 2 was obtained by alkaline hydrolysis of (+)-(1R,2S) -acridine 1,2-oxide 4.

引用

页码：2711 / 2714

页数：4

共 18 条

[1]

Agarwal S. K, 1986, TETRAHEDRON LETT, V26, P4253

[2] SYNTHESIS OF ARENE OXIDE AND TRANS-DIHYDRODIOL METABOLITES OF QUINOLINE [J].

AGARWAL, SK ;

BOYD, DR ;

DAVIES, RJH ;

HAMILTON, L ;

JERINA, DM ;

MCCULLOUGH, JJ ;

PORTER, HP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (07) :1969-1974

[3]

[Anonymous], 1986, SHELXS86 PROGRAM SOL

[4] A GENERAL-METHOD FOR THE RESOLUTION OF CYCLIC TRANS-BROMOHYDRIN ENANTIOMERS - ABSOLUTE-CONFIGURATION BY CRYSTAL-STRUCTURE ANALYSIS OF A 2-METHOXY-2-PHENYL-2-TRIFLUOROMETHYLACETATE (MTPA) DIASTEREOISOMER [J].

BALANI, SK ;

BOYD, DR ;

CASSIDY, ES ;

DEVINE, GI ;

MALONE, JF ;

MCCOMBE, KM ;

SHARMA, ND ;

JENNINGS, WB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (11) :2751-2756

[5] STRUCTURE AND STEREOCHEMISTRY OF CIS-DIHYDRO DIOL AND PHENOL METABOLITES OF BICYCLIC AZAARENES FROM PSEUDOMONAS-PUTIDA UV4 [J].

BOYD, DR ;

SHARMA, ND ;

DORRITY, MRJ ;

HAND, MV ;

MCMORDIE, RAS ;

MALONE, JF ;

PORTER, HP ;

DALTON, H ;

CHIMA, J ;

SHELDRAKE, GN .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (09) :1065-1071

[6] ARENE OXIDE-OXEPIN ISOMERIZATION - THEORETICAL PREDICTIONS AND EXPERIMENTAL-EVIDENCE [J].

BOYD, DR ;

STUBBS, ME .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2554-2559

[7] ABSOLUTE-CONFIGURATIONS OF THE ARENE OXIDE, TRANS-DIHYDRODIOL AND CIS-DIHYDRODIOL PRODUCTS RESULTING FROM METABOLISM OF QUINOLINE AT THE 5,6-BOND [J].

BOYD, DR ;

BUSHMAN, DR ;

DAVIES, RJH ;

DORRITY, MRJ ;

HAMILTON, L ;

JERINA, DM ;

LEVIN, W ;

MCCULLOUGH, JJ ;

MCMORDIE, RAS ;

MALONE, JF ;

PORTER, HP .

TETRAHEDRON LETTERS, 1991, 32 (25) :2963-2966

[8] SYNTHESIS AND SOLVOLYSIS OF ACRIDINE 1,2-OXIDE AND 3,4-OXIDE - CRYSTAL-STRUCTURE OF ACRIDINE 1,2-OXIDE [J].

BOYD, DR ;

DAVIES, RJH ;

HAMILTON, L ;

MCCULLOUGH, JJ ;

MALONE, JF ;

PORTER, HP ;

SMITH, A ;

CARL, JM ;

SAYER, JM ;

JERINA, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (05) :984-990

[9]

DONG M, 1978, CARCINOG COMPR SURV, V3, P97

[10]

JOHNSON CK, 1986, ORNL5138 REP

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