Chemical and enzyme-catalysed syntheses of enantiopure epoxide and diol derivatives of chromene, 2,2-dimethylchromene, and 7-methoxy-2,2-dimethylchromene (precocene-1)

被引：25

作者：

Boyd, DR ^{[1
]}

Sharma, ND ^{[1
]}

Boyle, R ^{[1
]}

Evans, TA ^{[1
]}

Malone, JF ^{[1
]}

McCombe, KM ^{[1
]}

Dalton, H ^{[1
]}

Chima, J ^{[1
]}

机构：

[1] UNIV WARWICK,DEPT BIOL SCI,COVENTRY CV4 7AL,W MIDLANDS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 14期

关键词：

D O I：

10.1039/p19960001757

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Procaryotic (bacterial) dioxygenase-catalysed asymmetric dihydroxylation of chromene and 2,2-dimethylchromene to yield the (4S)-enantiomers of the corresponding cis-diols exclusively is reported. The epoxide, and derived cis- and trans-diol products from the previously reported eucaryotic (mammalian) metabolism of precocene-1 (7-methoxy-2,2-dimethylchromene), and the corresponding epoxide and diol derivatives of chromene and 2,2-dimethylchromene, have now been obtained in enantiopure form by chemical resolution of the corresponding bromohydrins using methoxy(trifluoromethyl)phenylacetic acid (MTPA) or camphanate esters, The absolute configurations of the epoxides, cis- and trans-diols have been determined by chemical synthesis from, and stereochemical correlation with, the corresponding camphanate and MTPA esters, X-Ray crystal structure analysis has provided an unequivocal method for assignment of the absolute stereochemistry in each case.

引用

页码：1757 / 1765

页数：9

共 28 条

[11] STEREOCHEMISTRY AND REACTIONS OF SOME 3,4-DISUBSTITUTED CHROMANS [J].

COTTERIL.WD ;

COTTAM, J ;

LIVINGST.R .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (08) :1006-&

[12]

EVANS JM, 1991, CHEM BRIT, P439

[13] METABOLISM AND HEPATOTOXICITY OF THE NATURALLY-OCCURRING BENZO[B]PYRAN PRECOCENE-I [J].

HALPIN, RA ;

VYAS, KP ;

ELNAGGAR, SF ;

JERINA, DM .

CHEMICO-BIOLOGICAL INTERACTIONS, 1984, 48 (03) :297-315

[14] RESOLUTION AND ASSIGNMENT OF ABSOLUTE-CONFIGURATION TO THE (+)-CIS AND (-)-CIS AND TRANS 3,4-DIOL METABOLITES OF THE ANTI-JUVENILE HORMONE PRECOCENE-I [J].

HALPIN, RA ;

ELNAGGAR, SF ;

MCCOMBE, KM ;

VYAS, KP ;

BOYD, DR ;

JERINA, DM .

TETRAHEDRON LETTERS, 1982, 23 (16) :1655-1658

[15]

HANESSIAN S, 1993, J ORG CHEM, V115, P8463

[16] PREPARATION OF HOMOCHIRAL CHROMAN-4-OLS AND THIOCHROMAN-4-OLS BY MICROBIAL BIOTRANSFORMATION [J].

HOLLAND, HL ;

MANOHARAN, TS ;

SCHWEIZER, F .

TETRAHEDRON-ASYMMETRY, 1991, 2 (05) :335-338

[17] THE SYNTHESIS OF THE EPOXIDE AND SOME OTHER POSSIBLE METABOLITES OF PRECOCENE-I [J].

JENNINGS, RC ;

OTTRIDGE, AP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08) :1733-1738

[18]

KASTURI TR, 1967, TETRAHEDRON LETT, P2573

[19] REACTION OF SOME CHROMENS AND NAPHTHOPYRANS WITH BROMINE .2. [J].

LIVINGSTON, R .

JOURNAL OF THE CHEMICAL SOCIETY, 1962, (JAN) :76-&

[20] REACTION OF DICHLOROCARBENE WITH 2,3-CHROMENE AND 3,4-CHROMENE [J].

PARHAM, WE ;

HUESTIS, LD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) :813-&

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