An approach to the cephalotaxine ring skeleton using an ammonium ylide Stevens [1,2]-rearrangement

被引：28

作者：

Beall, LS ^{[1
]}

Padwa, A ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 24期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(98)00774-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ammonium ylides derived from the Cu(II)-catalyzed decomposition of alpha-diazo carbonyls tethered to tertiary amines underwent a benzylic Stevens [1,2]-rearrangement to give tetrahydro isoquinolines or benzazepines containing fused five-membered rings, a feature found in the cephalotaxus and lycorane alkaloids. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：4159 / 4162

页数：4

相关论文

共 29 条

[1] SYNTHETIC STUDIES ON SIDE-CHAINS OF CEPHALOTAXUS ESTERS [J].

BATES, RB ;

CUTLER, RS ;

FREEMAN, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (25) :4162-4164

[2] STEREOSPECIFIC SYNTHESIS OF THE CYCLOPENTA[E]PHENANTHRIDINE RING-SYSTEM - TETRACYCLIC AND PENTACYCLIC ANALOGS OF CEPHALOTAXUS ALKALOIDS [J].

BRYCE, MR ;

GARDINER, JM .

TETRAHEDRON, 1988, 44 (02) :599-612

[3]

CLARK JS, 1995, TETRAHEDRON LETT, V36, P2519

[4] SYNTHESIS OF CYCLIC ETHERS FROM COPPER CARBENOIDS BY FORMATION AND REARRANGEMENT OF OXONIUM YLIDES [J].

CLARK, JS ;

KROWIAK, SA ;

STREET, LJ .

TETRAHEDRON LETTERS, 1993, 34 (27) :4385-4388

[5] Cyclization of rhodium carbenoids using ester and amido carbonyl groups [J].

Curtis, EA ;

Worsencroft, KJ ;

Padwa, A .

TETRAHEDRON LETTERS, 1997, 38 (19) :3319-3322

[6] NEW ROUTES TO FUNCTIONALIZED BENZAZEPINE SUBSTRUCTURES - A NOVEL TRANSFORMATION OF AN ALPHA-DIKETONE THIOAMIDE INDUCED BY TRIMETHYL PHOSPHITE [J].

FANG, FG ;

MAIER, ME ;

DANISHEFSKY, SJ ;

SCHULTE, G .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) :831-838

[7] RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS [J].

GRUBBS, RH ;

MILLER, SJ ;

FU, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) :446-452

[8] STUDIES IN CEPHALOTAXUS ALKALOIDS - STEREOSPECIFIC TOTAL SYNTHESIS OF HOMOHARRINGTONINE [J].

HIRANUMA, S ;

SHIBATA, M ;

HUDLICKY, T .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (26) :5321-5326

[9]

HUANG L, 1984, ALKALOIDS CHEM PHARM, V23, pCH3

[10]

HUDLICKY T, 1987, ALKALOIDS CHEM BIOL, V5, pCH5