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

[1] SYNTHETIC APPROACHES TO THE ANGUCYCLINE ANTIBIOTICS - SYNTHESIS OF THE C-GLYCOSIDIC CD RING-SYSTEM [J].

ANDREWS, FL ;

LARSEN, DS .

TETRAHEDRON LETTERS, 1994, 35 (46) :8693-8696

[2] INHIBITION OF TYROSINE HYDROXYLASE BY AQUAYAMYCIN [J].

AYUKAWA, S ;

TAKEUCHI, T ;

SEZAKI, M ;

HARA, T ;

UMEZAWA, H ;

NAGATSU, T .

JOURNAL OF ANTIBIOTICS, 1968, 21 (05) :350-&

[3] AN EFFICIENT SYNTHESIS OF AKLAVINONE AND RELATED 11-DEOXYANTHRACYCLINONES [J].

BAUMAN, JG ;

HAWLEY, RC ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1569-1573

[4] FORMATION OF CYCLIC PEROXIDES BY OXYGENATION OF THIOPHENOL-DIENE MIXTURES [J].

BECKWITH, ALJ ;

WAGNER, RD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) :7099-7100

[5] REGIOSPECIFIC, STEREOSPECIFIC RING-CLOSURE OF ALKENYLPEROXYL RADICALS GENERATED BY OXYGENATION OF BENZENETHIOL-TRIENE MIXTURES [J].

BECKWITH, ALJ ;

WAGNER, RD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (11) :485-486

[6] REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY [J].

BECKWITH, ALJ ;

SCHIESSER, CH .

TETRAHEDRON, 1985, 41 (19) :3925-3941

[7] EFFECT OF ALLYLIC SUBSTITUENTS ON THE FACE SELECTIVITY OF DIELS-ALDER REACTIONS OF SEMICYCLIC DIENES [J].

DATTA, SC ;

FRANCK, RW ;

TRIPATHY, R ;

QUIGLEY, GJ ;

HUANG, L ;

CHEN, S ;

SIHAED, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8472-8478

[8] ON THE INTRAMOLECULARITY OF THE VITAMIN-K MODEL OXIDATION [J].

DOWD, P ;

HAM, SW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9403-9404

[9] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].

EVANS, DA ;

CHAPMAN, KT ;

CARREIRA, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578

[10]

FELDMAN KS, 1995, SYNLETT, P217

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