SYNTHETIC STUDIES OF THE ANGUCYCLINE ANTIBIOTICS - STEREOCONTROLLED ASSEMBLY OF THE SF 2315B RING-SYSTEM

被引：46

作者：

KIM, K ^{[1
]}

GUO, Y ^{[1
]}

SULIKOWSKI, GA ^{[1
]}

机构：

[1] TEXAS A&M UNIV,DEPT CHEM,COLLEGE STN,TX 77843

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 21期

关键词：

D O I：

10.1021/jo00126a043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereocontrolled assembly of epoxy quinol 2 is described. Diels-Alder cycloaddition between 2-bromo-5-acetoxyjuglone (5) and 3-[(triisopropylsilyl)oxy]-1-vinylcyclohexene (6c) followed by saponification provided quinone 11b in good overall yield. Oxygenation of a tetrahydrofuran solution of 11b in the presence of tetrabutylammonium fluoride resulted in the production of epoxy alcohols alpha-12b and alpha-13b. Epoxy alcohol alpha-12b was converted to epoxy quinol 2 in five steps. A key transformation of the latter reaction sequence was a C1 hydroxyl-directed reduction of the C12 keto group (20 --> 21). The assigned structure of 2 was confirmed by single-crystal X-ray analysis.

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页码：6866 / 6871

页数：6

相关论文

共 34 条

[11] REACTION OF THE QUINONE METHIDE FROM REDUCTIVE GLYCOSIDIC CLEAVAGE OF DAUNOMYCIN WITH MOLECULAR-OXYGEN - EVIDENCE FOR SEMIQUINONE METHIDE FORMATION [J].

GAUDIANO, G ;

KOCH, TH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) :9423-9425

[12] STUDIES IN THE BENZANNULATION OF A CYCLOALKYNONE - AN APPROACH TO THE SYNTHESIS OF ANTIBIOTICS CONTAINING THE BENZ[A]ANTHRACENE CORE STRUCTURE [J].

GORDON, DM ;

DANISHEFSKY, SJ ;

SCHULTE, GK .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7052-7055

[13] A NEW ROUTE FOR THE EFFICIENT SYNTHESIS OF (+/-)OCHROMYCINONE, A NATURALLY-OCCURRING BENZ[A]ANTHRAQUINONE [J].

GUINGANT, A ;

BARRETO, MM .

TETRAHEDRON LETTERS, 1987, 28 (27) :3107-3110

[14] STUDIES ON THE ISOTETRACENONE ANTIBIOTICS .2. KERRIAMYCIN-A, KERRIAMYCIN-B, AND KERRIAMYCIN-C NEW ANTITUMOR ANTIBIOTICS [J].

HAYAKAWA, Y ;

IWAKIRI, T ;

IMAMURA, K ;

SETO, H ;

OTAKE, N .

JOURNAL OF ANTIBIOTICS, 1985, 38 (07) :960-963

[15] REGIOSPECIFIC SYNTHESIS OF BROMOJUGLONE DERIVATIVES [J].

HEINZMAN, SW ;

GRUNWELL, JR .

TETRAHEDRON LETTERS, 1980, 21 (45) :4305-4308

[16] DERIVATIVES OF SAQUAYAMYCIN-A AND SAQUAYAMYCIN-B REGIOSELECTIVE AND DIASTEREOSELECTIVE ADDITION OF ALCOHOLS TO THE L-ACULOSE MOIETY [J].

HENKEL, T ;

ZEECK, A .

JOURNAL OF ANTIBIOTICS, 1990, 43 (07) :830-837

[17] MECHANISM OF BROMINATION OF 1,5-DIACETOXYNAPHTHALENE [J].

JUNG, ME ;

HAGENAH, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (26) :5359-5361

[18] DIRECTED ORTHO METALATION REACTIONS - CONVERGENT SYNTHESIS OF ANGULAR ANTHRACYCLINONES OCHROMYCINONE AND X-14881 C [J].

KATSUURA, K ;

SNIECKUS, V .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (01) :124-130

[19]

KAWASHIMA A, 1989, CHEM PHARM BULL, V37, P3429

[20] SYNTHETIC STUDIES OF THE ANGUCYCLINE ANTIBIOTICS - REACTION OF A QUINONE METHIDE PRODUCED FROM A BENZ[A]ANTHRACENE WITH MOLECULAR-OXYGEN [J].

KIM, KJ ;

REIBENSPIES, J ;

SULIKOWSKI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) :5557-5559

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