Haem d(1): stereoselective synthesis of the reduced form of its parent macrocycle using the original coupling strategy

被引：16

作者：

Aucken, CJ ^{[1
]}

Leeper, FJ ^{[1
]}

Battersby, AR ^{[1
]}

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 14期

关键词：

D O I：

10.1039/a700652g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A substituted isobacteriochlorin, which corresponds structurally to the reduced metal-free macrocycle of haem d(1), has been synthesised by a stereoselective route in which the final step is a photochemical 18 pi-electron antarafacial cyclisation of an open-chain precursor.

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页码：2099 / 2109

页数：11

相关论文

共 33 条

[1] SYNTHESIS OF 20-METHYL AND 20-CYANO ISOBACTERIOCHLORINS - THE WITTIG-PHOTOCHEMICAL APPROACH [J].

ARNOTT, DM ;

BATTERSBY, AR ;

HARRISON, PJ ;

HENDERSON, GB ;

SHENG, ZC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (08) :525-526

[2] BIOSYNTHESIS OF VITAMIN-B12 [J].

BATTERSBY, AR .

ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (05) :147-152

[3] SYNTHETIC STUDIES RELEVANT TO BIOSYNTHETIC RESEARCH ON VITAMIN-B12 .5. SYNTHESIS OF (RS)-RING-B IMIDE [J].

BATTERSBY, AR ;

WESTWOOD, SW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (08) :1679-1687

[4] SYNTHETIC STUDIES RELEVANT TO BIOSYNTHETIC RESEARCH ON VITAMIN-B12 .11. MODIFICATION OF THE EAST AND WEST BUILDING-BLOCKS AND STUDY OF DIFFERENT ASSEMBLY METHODS FOR SYNTHESIS OF ISOBACTERIOCHLORINS [J].

BATTERSBY, AR ;

BLOCK, MH ;

LEEPER, FJ ;

ZIMMERMAN, SC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (17) :2189-2195

[5] SYNTHETIC STUDIES RELEVANT TO BIOSYNTHETIC RESEARCH ON VITAMIN-B12 .8. SYNTHESIS OF (+/-)-FAKTOR-I OCTAMETHYL ESTER [J].

BATTERSBY, AR ;

TURNER, SPD ;

BLOCK, MH ;

SHENG, ZC ;

ZIMMERMAN, SC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (06) :1577-1586

[6] SYNTHETIC STUDIES RELEVANT TO BIOSYNTHETIC RESEARCH ON VITAMIN-B12 .10. CONSTRUCTION OF THE EAST AND WEST BUILDING-BLOCKS FOR SYNTHESIS OF ISOBACTERIOCHLORINS [J].

BATTERSBY, AR ;

BLOCK, MH ;

FOOKES, CJR ;

HARRISON, PJ ;

HENDERSON, GB ;

LEEPER, FJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (17) :2175-2187

[7]

BATTERSBY AR, 1979, J CHEM SOC PERK T 1, P1927, DOI 10.1039/p19790001927

[8] SYNTHESES RELEVANT TO VITAMIN-B12 BIOSYNTHESIS - SYNTHESIS OF SIROHYDROCHLORIN AND OF ITS OCTAMETHYL ESTER [J].

BLOCK, MH ;

ZIMMERMAN, SC ;

HENDERSON, GB ;

TURNER, SPD ;

WESTWOOD, SW ;

LEEPER, FJ ;

BATTERSBY, AR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (16) :1061-1063

[9] EVIDENCE THAT HEME D1 IS A 1,3-PORPHYRINDIONE [J].

CHANG, CK ;

TIMKOVICH, R ;

WU, W .

BIOCHEMISTRY, 1986, 25 (26) :8447-8453

[10] SYNTHESIS AND CHARACTERIZATION OF ALKYLATED ISOBACTERIOCHLORINS, MODELS OF SIROHEME AND SIROHYDROCHLORIN [J].

CHANG, CK .

BIOCHEMISTRY, 1980, 19 (09) :1971-1976

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