2,2-Dimethyl cyclopentanones by acid catalyzed ring expansion of isopropenylcyclobutanols.: A short synthesis of (±)-α-cuparenone and (±)-herbertene

被引：30
作者：
Bernard, AM [1 ]
Frongia, A [1 ]
Secci, F [1 ]
Piras, PP [1 ]
机构：
[1] Univ Cagliari, Dipartimento Sci Chim, I-09042 Cagliari, Italy
来源：
CHEMICAL COMMUNICATIONS | 2005年 / 30期
关键词：
D O I：
10.1039/b505707h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
2,2-Dimethyl cyclopentanones are readily prepared by acid catalyzed ring expansion of isopropenylcyclobutanols; the method allows ready access to the family of sesquiterpenes cuparanes and herbertanes, as demonstrated by the synthesis of (+/-)-alpha-cuparenone and the direct precursor of (+/-)-herbertene.
引用
收藏
页码：3853 / 3855
页数：3
相关论文
共 36 条
  • [1] Synthesis of (S)-(-)-β-cuparenone and (S)-(-)-cuparene
    Aavula, BR
    Cui, Q
    Mash, EA
    [J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (23) : 4681 - 4686
  • [2] Enantioselective synthesis of natural (-)-tochuinyl acetate, (-)-dihydrotochuinyl acetate and (+)-β-cuparenone using both enantiomers of the same building block
    Acherar, S
    Audran, G
    Cecchin, F
    Monti, H
    [J]. TETRAHEDRON, 2004, 60 (28) : 5907 - 5912
  • [3] Use of lipase-catalyzed kinetic resolution for the enantioselective approach toward sesquiterpenes containing quaternary centers: the cuparane family
    Acherar, S
    Audran, G
    Vanthuyne, N
    Monti, H
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (16) : 2413 - 2418
  • [4] Use of cyclobutyl derivatives as intermediates in the synthesis of 1,2a,3,8b-tetrahydro-2H-cyclobuta[c]chromenes
    Bernard, AM
    Floris, C
    Frongia, A
    Piras, PP
    Secci, F
    [J]. TETRAHEDRON, 2004, 60 (02) : 449 - 457
  • [5] Unexpected stereochemistry in the lithium salt catalyzed ring expansion of nonracemic oxaspiropentanes.: Formal syntheses of (-)-(4R,5R)-muricatacin and the pheromone (R)-japonilure
    Bernard, AM
    Frongia, A
    Piras, PP
    Secci, F
    [J]. ORGANIC LETTERS, 2003, 5 (16) : 2923 - 2926
  • [6] Synthesis of new heterocycles through a cation-driven tandem ring-enlargement-annulation reaction
    Bernard, AM
    Cadoni, E
    Frongia, A
    Piras, PP
    Secci, F
    [J]. ORGANIC LETTERS, 2002, 4 (15) : 2565 - 2567
  • [7] Synthesis of tertiary cyclobutanols through stereoselective ring expansion of oxaspiropentanes induced by Grignard reagents
    Bernard, AM
    Floris, C
    Frongia, A
    Piras, PP
    [J]. TETRAHEDRON, 2000, 56 (26) : 4555 - 4563
  • [8] CAROTENOIDS AND RELATED-COMPOUNDS .37. STEREOCHEMISTRY AND SYNTHESIS OF CAPSORUBIN
    BOWDEN, RD
    COOPER, RDG
    HARRIS, CJ
    MOSS, GP
    WEEDON, BCL
    JACKMAN, LM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (07): : 1465 - 1474
  • [9] An efficient synthesis of (±)-β-herbertenol by a 1,3-cyclopentadione annelation strategy
    Chavan, SP
    Kharul, RK
    Kale, RR
    Khobragade, DA
    [J]. TETRAHEDRON, 2003, 59 (15) : 2737 - 2741
  • [10] SULFUR-ASSISTED RING EXPANSION OF THE POTASSIUM-SALTS OF 1-VINYLCYCLOBUTANOLS - A VERSATILE SYNTHESIS OF CYCLOHEXANONES
    COHEN, T
    YU, LC
    DANIEWSKI, WM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) : 4596 - 4600
1234