PtCl2-catalyzed transannular cycloisomerization of 1,5-enynes:: A new efficient regio- and stereocontrolled access to tricyclic derivatives

被引:67
作者
Blaszykowski, C [1 ]
Harrak, Y [1 ]
Gonçalves, MH [1 ]
Cloarec, JM [1 ]
Dhimane, AL [1 ]
Fensterbank, L [1 ]
Malacria, M [1 ]
机构
[1] Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
关键词
D O I
10.1021/ol048463n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(GRAPHICS) Transannular PtCL2-catalyzed cycloisomerizations open a new route to cyclopropanic tricyclic systems. Ketones A or C were efficiently prepared from the same cycloundec-5-en-1-yne precursor B, depending on the substituent at the propargylic position (either benzoate or methoxy).
引用
收藏
页码:3771 / 3774
页数:4
相关论文
共 42 条
  • [11] Elliott MR, 1997, J AM CHEM SOC, V119, P3427
  • [12] Elliott MR, 2000, EUR J ORG CHEM, V2000, P155
  • [13] FAVELANONE, A NOVEL TETRACYCLIC CYCLOPROPANE DERIVATIVE FROM THE BRAZILIAN PLANT, CNIDOSCOLUS-PHYLLACANTHUS
    ENDO, Y
    OHTA, T
    NOZOE, S
    [J]. TETRAHEDRON LETTERS, 1991, 32 (40) : 5555 - 5558
  • [14] Platinum-catalyzed cycloisomerization reactions of enynes
    Fürstner, A
    Stelzer, F
    Szillat, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (48) : 11863 - 11869
  • [15] Free radical-mediated macrocyclisations and transannular cyclisations in synthesis
    Handa, S
    Pattenden, G
    [J]. CONTEMPORARY ORGANIC SYNTHESIS, 1997, 4 (03): : 196 - 215
  • [16] ORGANOMETALLIC REAGENTS IN ORGANIC-SYNTHESIS .8. ORGANOCUPRATES AS ELECTRON-TRANSFER REAGENTS - EVALUATION FOR CONJUGATE ADDITION OF ELECTROPHILES TO ALPHA,BETA-UNSATURATED KETONES
    HANNAH, DJ
    SMITH, RAJ
    TEOH, I
    WEAVERS, RT
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (01) : 181 - 188
  • [17] PtCl2-catalyzed cycloisomerizations of 5-En-1-yn-3-ol systems
    Harrak, Y
    Blaszykowski, C
    Bernard, M
    Cariou, K
    Mainetti, E
    Mouriès, V
    Dhimane, AL
    Fensterbank, L
    Malacria, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) : 8656 - 8657
  • [18] Biotransformation of shiromodiol diacetate, myli-4(15)-en-9-one and myliol by Aspergillus niger
    Hayashi, K
    Asano, K
    Tanaka, M
    Takaoka, D
    Nozaki, H
    [J]. PHYTOCHEMISTRY, 1998, 48 (03) : 461 - 466
  • [20] REACTIONS OF TRANSITION-METAL COMPOUNDS WITH MACROCYCLIC ALKADIYNES .4. INTRAMOLECULAR TRANSANNULAR CYCLIZATIONS WITH CYCLOPENTADIENYLDICARBONYLRHODIUM
    KING, RB
    ACKERMAN.MN
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 67 (03) : 431 - 441