Diastereoselective SmI2-mediated cascade radical cyclisations of methylenecyclopropane derivatives -: a synthesis of paeonilactone B

被引:31
作者
Boffey, RJ
Santagostino, M
Whittingham, WG
Kilburn, JD [1 ]
机构
[1] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England
[2] Zeneca Agrochem, Jealotts Hill Res Stn, Bracknell RG42 6ET, Berks, England
关键词
D O I
10.1039/a804297g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The SmI2-mediated cascade reaction of methylenecyclopropyl ketone 9 proceeds with high diastereoselectivity, which is critically dependent on the presence of HMPA, and provides a short route to paeonilactone B.
引用
收藏
页码:1875 / 1876
页数:2
相关论文
共 16 条
  • [1] Some novel electron transfer mediated cascade ring-opening reactions of bicyclo[4.1.0]ketones
    Batey, RA
    Harling, JD
    Motherwell, WB
    [J]. TETRAHEDRON, 1996, 52 (35) : 11421 - 11444
  • [2] SYNTHESIS OF AMPHOTERICIN-B .2. FRAGMENT C-D OF THE AGLYCONE
    BOSCHELLI, D
    TAKEMASA, T
    NISHITANI, Y
    MASAMUNE, S
    [J]. TETRAHEDRON LETTERS, 1985, 26 (43) : 5239 - 5242
  • [3] AN EFFICIENT SYNTHESIS OF MONOTERPENE ALPHA-METHYLENE-GAMMA-BUTYROLACTONES
    BROCKSOM, TJ
    DOSSANTOS, RB
    VARANDA, NA
    BROCKSOM, U
    [J]. SYNTHETIC COMMUNICATIONS, 1988, 18 (12) : 1403 - 1410
  • [4] ALKYL RADICAL CYCLIZATIONS OF METHYLENECYCLOPROPANE DERIVATIVES
    DESTABEL, C
    KILBURN, JD
    KNIGHT, J
    [J]. TETRAHEDRON, 1994, 50 (38) : 11267 - 11288
  • [5] A SAMARIUM(II) IODIDE PROMOTED TANDEM RADICAL CYCLIZATION - THE TOTAL SYNTHESIS OF (+/-)-HYPNOPHILIN AND THE FORMAL SYNTHESIS OF (+/-)-CORIOLIN
    FEVIG, TL
    ELLIOTT, RL
    CURRAN, DP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (15) : 5064 - 5067
  • [6] TOTAL SYNTHESES OF (+)-PAEONILACTONE-B AND (-)-PAEONISUFFRONE
    HATAKEYAMA, S
    KAWAMURA, M
    MUKUGI, Y
    IRIE, H
    [J]. TETRAHEDRON LETTERS, 1995, 36 (02) : 267 - 268
  • [7] PAEONILACTONE-A, PAEONILACTONE-B, AND PAEONILACTONE-C, NEW MONOTERPENOIDS FROM PAEONY ROOT
    HAYASHI, T
    SHINBO, T
    SHIMIZU, M
    ARISAWA, M
    MORITA, N
    KIMURA, M
    MATSUDA, S
    KIKUCHI, T
    [J]. TETRAHEDRON LETTERS, 1985, 26 (31) : 3699 - 3702
  • [8] ACYCLIC STEREOSELECTION .25. STEREOSELECTIVE SYNTHESIS OF THE C-1 TO C-7 MOIETY OF ERYTHRONOLIDE-A
    HEATHCOCK, CH
    YOUNG, SD
    HAGEN, JP
    PILLI, R
    BADERTSCHER, U
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (12) : 2095 - 2105
  • [9] STUDIES IN STEREOCHEMISTRY .32. MECHANISM OF ELIMINATION OF SULFOXIDES
    KINGSBURY, CA
    CRAM, DJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (07) : 1810 - 1819
  • [10] Selective preparation of complex polycyclic molecules from acyclic precursors via radical mediated- or transition metal-catalyzed cascade reactions
    Malacria, M
    [J]. CHEMICAL REVIEWS, 1996, 96 (01) : 289 - 306