PHENOL OXIDATION AND BIOSYNTHESIS .27. REACTIONS OF RELEVANCE TO THE FORMATION OF ERYSODIENONE INVITRO

被引:9
作者
BARRETT, AGM [1 ]
BARTON, DHR [1 ]
FRANCKOWIAK, G [1 ]
PAPAIOANNOU, D [1 ]
WIDDOWSON, DA [1 ]
机构
[1] UNIV LONDON IMPERIAL COLL SCI & TECHNOL,DEPT CHEM,LONDON SW7 2AY,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 03期
关键词
D O I
10.1039/p19790000662
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Potassium hexacyanoferrate(III) oxidation of N-(2-arylethyl)-2- arylacetamide and arylmethyl arylpropyl ketone gave the corresponding nine-membered ring derivatives formed by p,p-phenol oxidative coupling (where aryl was 3-hydroxy-4-methoxyphenyl). This strongly supports the previously reported mechanism for the in vitro formation of erysodienone. The required ketone was prepared from O-benzylisovanillin by homologation with toluene-4-sulphonylmethyl isonitrile.
引用
收藏
页码:662 / 668
页数:7
相关论文
共 30 条
  • [1] PHENOL OXIDATION AND BIOSYNTHESIS .26. ISONITRILES IN THE SYNTHESIS OF BENZYLISOQUINOLINE DERIVATIVES
    BARRETT, AGM
    BARTON, DHR
    FALCK, JR
    PAPAIOANNOU, D
    WIDDOWSON, DA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (03): : 652 - 661
  • [2] BARTON DHR, 1973, J CHEM SOC CHEM COMM, P781
  • [3] PHENOL OXIDATION AND BIOSYNTHESIS .20. MECHANISM OF ERYSODIENONE FORMATION IN-VITRO
    BARTON, DHR
    BOAR, RB
    WIDDOWSO.DA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (09): : 1208 - &
  • [4] SOME REACTIONS OF SOFT ELECTROPHILES WITH ESTERS AND OTHER COMPOUNDS CONTAINING THIOCARBONYL GROUP
    BARTON, DHR
    STICK, RV
    SUBRAMANIAN, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (19): : 2112 - 2116
  • [5] SYNTHESES ALONG BIOSYNTHETIC PATHWAYS .I. SYNTHESIS OF (+)-ISOTHEBAINE
    BATTERSBY, AR
    BROWN, TH
    CLEMENTS, JH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1965, (AUG): : 4550 - +
  • [6] BRACHO RD, 1974, THESIS LONDON
  • [7] ISOQUINOLINE SYNTHESES .225. SYNTHESES OF 7-HYDROXY-6-METHOXY-2-METHYL-1-(4-HYDROXY-3,5-DIMETHOXYPHENETHYL)-1,2,3,4-TETRAHYDROISOQUINOLINE AN IMPORTANT INTERMEDIATE IN HOMOAPOMORPHINE ALKALOID SYNTHESIS
    BROSSI, A
    VANBURIK, J
    TEITEL, S
    [J]. HELVETICA CHIMICA ACTA, 1968, 51 (08) : 1965 - &
  • [8] WITTIG REACTIONS WITH AID OF ETHYLENE OXIDE
    BUDDRUS, J
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (07) : 536 - &
  • [9] DEMLOW EV, 1974, ANGEW CHEM, V86, P187
  • [10] DOCKX J, 1973, SYNTHESIS-STUTTGART, P441