TOTAL SYNTHESIS OF PHENANTHROVIRIDIN AGLYCON - THE 1ST NATURALLY-OCCURRING BENZO[B]PHENANTHRIDINE

被引：50

作者：

GORE, MP ^{[1
]}

GOULD, SJ ^{[1
]}

WELLER, DD ^{[1
]}

机构：

[1] OREGON STATE UNIV,DEPT CHEM,CORVALLIS,OR 97331

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 07期

关键词：

D O I：

10.1021/jo00007a009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of a naturally occurring benzo[b]phenanthridine has been accomplished via coupling of a cyanophthalide and a substituted bromocinnamate and subsequent transformation of the resulting aryl naphthoquinone carboxylate via formylation, Hoffmann rearrangement, cyclization, and deprotection steps.

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页码：2289 / 2291

页数：3

相关论文

共 66 条

[11] SYNTHESIS OF FUNCTIONALIZED HYDROXYPHTHALIDES AND THEIR CONVERSION TO 3-CYANO-1(3H)-ISOBENZOFURANONES - THE DIELS-ALDER REACTION OF METHYL 4,4-DIETHOXYBUTYNOATE AND CYCLOHEXADIENES [J].

FRESKOS, JN ;

MORROW, GW ;

SWENTON, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (06) :805-810

[12] REARRANGEMENT OF A 4,4-DISUBSTITUTED HOMOPHTHALIMIDE TO BENZO(B]PHENANTHRIDINE SYSTEM [J].

GENSLER, WJ ;

VINOVSKI.M ;

WANG, N .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (11) :3664-&

[13] 2-(TRIMETHYLSILYL)ETHYL ESTERS AS CARBOXYL PROTECTING GROUP - APPLICATION IN SYNTHESIS OF (-)-(S)-CURVULARIN [J].

GERLACH, H .

HELVETICA CHIMICA ACTA, 1977, 60 (08) :3039-3044

[14] THE TIMING OF AROMATIC DEOXYGENATION IN AFLATOXIN BIOSYNTHESIS [J].

GRAYBILL, TL ;

PAL, K ;

MCGUIRE, SM ;

BROBST, SW ;

TOWNSEND, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8306-8308

[15]

HARTFORD WH, 1958, CHEM REV, V1, P1

[16] TOTAL SYNTHESIS OF THE CHARTREUSIN AGLYCON [J].

HAUSER, FM ;

COMBS, DW .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (21) :4071-4073

[17] TOTAL SYNTHESES OF (+/-)-DAUNOMYCINONE - REGIOSPECIFIC PREPARATIONS OF (+/-)-7,9-DIDEOXYDAUNOMYCINONE AND 6,11-DIHYDROXY-4-METHOXY-7,8,9,10-TETRAHYDRONAPHTHACENE-5,9,12-TRIONE [J].

HAUSER, FM ;

PRASANNA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (21) :6378-6386

[18]

HAUSER FM, 1982, J ORG CHEM, V47, P383, DOI 10.1021/jo00341a050

[19] SYNTHETIC STUDIES ON ANTHRACYCLINES [J].

HAUSER, FM ;

PRASANNA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (14) :2596-2598

[20] ANTHRA[1,2-B]PYRAN ANTIBIOTICS - TOTAL SYNTHESIS OF O-METHYLKIDAMYCINONE [J].

HAUSER, FM ;

RHEE, RP .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (15) :3061-3068

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