Morphine alkaloids. Part 142. Isomerization reactions of 7-substituted 6,14-bridged thebaine derivatives (Bentley compounds)

被引：6

作者：

Marton, J

Garadnay, S

Szabo, Z

Hosztafi, S

Makleit, S

机构：

[1] Lajos Kossuth Univ, Dept Organ Chem, H-4010 Debrecen, Hungary

[2] ICN Alkaloida Hungary Co Ltd, Res Dept, H-4440 Tiszavasvari, Hungary

[3] Royal Inst Technol, Dept Chem, S-10044 Stockholm, Sweden

来源：

ACTA CHEMICA SCANDINAVICA | 1998年 / 52卷 / 10期

关键词：

D O I：

10.3891/acta.chem.scand.52-1234

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Equilibration of the 7 alpha-->7 beta isomers of 7-substituted 6,14-ethenomorphinanes has been accomplished, for the first time, in dipolar aprotic solvents by the application of bases with weak nucleophilic character. Transformation of the 7 beta-nitrile with phenylmagnesium bromide led to a new type of 6,6 '-dimeric compound.

引用

收藏

页码：1234 / 1238

页数：5

相关论文

共 16 条

[1] ACID-CATALYZED REARRANGEMENTS IN THE NEPENTHONE SERIES [J].

BENTLEY, KW ;

BALL, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (11) :1720-1725

[2] NOVEL ANALGESICS AND MOLECULAR REARRANGEMENTS IN MORPHINE-THEBAINE GROUP .I. KETONES DERIVED FROM 6,14-ENDO-ETHENOTETRAHYDROTHEBAINE [J].

BENTLEY, KW ;

HARDY, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (13) :3267-&

[3] BASE-CATALYZED REARRANGEMENTS IN THE NEPENTHONE SERIES [J].

BENTLEY, KW ;

BALL, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (11) :1725-1730

[4] NOVEL ANALGESICS AND MOLECULAR REARRANGEMENTS IN MORPHINE-THEBAINE GROUP .2. ALCOHOLS DERIVED FROM 6,14-ENDO-ETHENO- AND 6,14-ENDO-ETHANOTETRAHYDROTHEBAINE [J].

BENTLEY, KW ;

HARDY, DG ;

MEEK, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (13) :3273-&

[5] NOVEL ANALGESICS AND MOLECULAR REARRANGEMENTS IN MORPHINE-THEBAINE GROUP .6. BASE-CATALYZED REARRANGEMENTS IN 6,14-ENDO-ETHENOTETRAHYDROTHEBAINE SERIES [J].

BENTLEY, KW ;

HARDY, DG ;

CROCKER, HP ;

HADDLESEY, DI ;

MAYOR, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (13) :3312-+

[6]

BENTLEY KW, 1971, ALKALOIDS DIELSALDER, P75

[7]

Casy A.F., 1986, Opioid Analgesics. Chemistry and Receptors, P69

[8] NUCLEAR MAGNETIC RESONANCE STUDIES IN 6,14-ENDO-ETHENOTETRAHYDROTHEBAINE SERIES [J].

FULMOR, W ;

LANCASTER, JE ;

MORTON, GO ;

BROWN, JJ ;

HOWELL, CF ;

NORA, CT ;

HARDY, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (13) :3322-+

[9] BUPRENORPHINE - REVIEW OF ITS PHARMACOLOGICAL PROPERTIES AND THERAPEUTIC EFFICACY [J].

HEEL, RC ;

BROGDEN, RN ;

SPEIGHT, TM ;

AVERY, GS .

DRUGS, 1979, 17 (02) :81-110

[10]

HERZ A, 1977, ARZNEIMITTEL-FORSCH, V27-2, P1865