ORGANOMETALLIC ADDITIONS TO PROTECTED QUINONE BIS-EPOXIDES AND QUINONE MONOACETALS - SYNTHESIS OF THE ARANOROSIN NUCLEUS

被引：18

作者：

MCKILLOP, A ^{[1
]}

TAYLOR, RJK ^{[1
]}

WATSON, RJ ^{[1
]}

LEWIS, N ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,TONBRIDGE TN11 9AN,KENT,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1992年 / 21期

关键词：

D O I：

10.1039/c39920001589

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The addition reactions of organometallic reagents to monoprotected quinone bis-epoxides 7 and quinone monoacetals 5 provide a route to the highly oxygenated cyclohexanols 2 and 3; the application of this methodology to the preparation of the aranorosin analogue 4 is described.

引用

页码：1589 / 1591

页数：3

共 13 条

[1]

BUCHI G, 1969, J ORG CHEM, V34, P1122

[2] ARANOROSIN, A NOVEL ANTIBIOTIC FROM PSEUDOARACHNIOTUS-ROSEUS .2. STRUCTURE ELUCIDATION [J].

FEHLHABER, HW ;

KOGLER, H ;

MUKHOPADHYAY, T ;

VIJAYAKUMAR, EKS ;

ROY, K ;

RUPP, RH ;

GANGULI, BN .

JOURNAL OF ANTIBIOTICS, 1988, 41 (12) :1785-1794

[3] STRUCTURE OF ARANOROSIN, A NEW ANTIBIOTIC OF A NOVEL SKELETAL TYPE [J].

FEHLHABER, HW ;

KOGLER, H ;

MUKHOPADHYAY, T ;

VIJAYAKUMAR, EKS ;

GANGULI, BN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) :8242-8244

[4]

GANEM B, 1990, CHEMTRACTS ORGANIC C, V3, P381

[5]

GREENE TW, 1991, PROTECTIVE GROUPS OR

[6]

KELLER R, Patent No. 3045680

[7] PD(II)-CATALYZED ACETAL KETAL HYDROLYSIS EXCHANGE-REACTIONS [J].

LIPSHUTZ, BH ;

POLLART, D ;

MONFORTE, J ;

KOTSUKI, H .

TETRAHEDRON LETTERS, 1985, 26 (06) :705-708

[8]

MCKILLOP A, 1992, SYNLETT, P201

[9]

RAO AVR, 1991, TETRAHEDRON LETT, V32, P6613

[10] ARANOROSIN, A NOVEL ANTIBIOTIC FROM PSEUDOARACHNIOTUS-ROSEUS .1. TAXONOMY, FERMENTATION, ISOLATION, CHEMICAL AND BIOLOGICAL PROPERTIES [J].

ROY, K ;

MUKHOPADHYAY, T ;

REDDY, GCS ;

DESIKAN, KR ;

RUPP, RH ;

GANGULI, BN .

JOURNAL OF ANTIBIOTICS, 1988, 41 (12) :1780-1784

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