Synthesis of Nororipavine and Noroxymorphone via N- and O-Demethylation of Iron Tricarbonyl Complex of Thebaine

被引：7

作者：

Machara, Ales ^{[1
]}

Endoma-Arias, Mary Ann A. ^{[2
,3
]}

Cisarova, Ivana ^{[4
]}

Cox, D. Phillip ^{[5
]}

Hudlicky, Tomas ^{[2
,3
]}

机构：

[1] Charles Univ Prague, Fac Sci, Dept Organ Chem, Hlavova 8, Prague 12843 2, Czech Republic

[2] Brock Univ, Dept Chem, 1812 Sir Isaac Brock Way, St Catharines, ON L2S 3A1, Canada

[3] Brock Univ, Ctr Biotechnol, 1812 Sir Isaac Brock Way, St Catharines, ON L2S 3A1, Canada

[4] Charles Univ Prague, Fac Sci, Dept Inorgan Chem, Hlavova 8, Prague 12843 2, Czech Republic

[5] Noramco Inc, 503 Carr Rd,Suite 200, Wilmington, DE 19809 USA

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 12期

基金：

加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

alkaloids; iron-diene complexes; nororipavine synthesis; iron decomplexation; demethylation; CATALYZED OXIDATIVE AMIDATION; MOLECULAR-REARRANGEMENTS; MORPHINE ALKALOIDS; OPIUM-ALKALOIDS; TERTIARY-AMINES; ORIPAVINE; ACID; DERIVATIVES; ANALGESICS; NALTREXONE;

D O I：

10.1055/s-0035-1561435

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thebaine was converted into its iron tricarbonyl complex, which underwent successive N- and O-demethylation with BrCN and BBr3, respectively. Decomplexation of the iron tricarbonyl moiety was accomplished with ammonium cerium(IV) nitrate (CAN) and base-catalyzed hydrolysis furnished nororipavine. When excess CAN was used the methoxydiene unit was converted into its C-14 nitrate that on hydrogenation and further hydrolysis furnished noroxymorphone. Full experimental and spectral data are provided for all key compounds.

引用

页码：1803 / 1813

页数：11

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