STERIC CONTROL-BASED ON ALKYL SUBSTITUENTS IN THE [2,3]SIGMATROPIC REARRANGEMENT OF 9-MEMBERED ALLYLSULFONIUM YLIDES - A NEW ENTRY TO THE STEREOSELECTIVE SYNTHESIS OF ELEMANE-TYPE SESQUITERPENOIDS

被引:7
作者
KIDO, F
YAMAJI, K
SINHA, SC
YOSHIKOSHI, A
KATO, M
机构
关键词
D O I
10.1039/c39940000789
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The rhodium(II)-catalysed cyclisation of acyclic alpha-diazomalonate 1b and alpha-diazo-beta-keto esters 1c, d give stereoselectively the highly substituted delta-lactone 3b and cyclohexanones 3c, d, respectively, by [2,3]sigmatropic rearrangement via the stereocontrolled nine-membered allylsulfonium ylides 2b-d.
引用
收藏
页码:789 / 790
页数:2
相关论文
共 17 条
  • [1] ANDO W, 1977, ACCOUNTS CHEM RES, V10, P178
  • [2] CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS
    DOYLE, MP
    [J]. CHEMICAL REVIEWS, 1986, 86 (05) : 919 - 939
  • [3] THE USE OF 4,4-DISUBSTITUTED NOPINONES FOR NATURAL-PRODUCT SYNTHESIS - SYNTHESIS OF ELEMANOID SESQUITERPENES
    KATO, M
    WATANABE, M
    VOGLER, B
    AWEN, BZ
    MASUDA, Y
    TOOYAMA, Y
    YOSHIKOSHI, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) : 7071 - 7076
  • [4] KIDO F, 1993, J CHEM RES-S, P18
  • [5] KIDO F, 1991, HETEROCYCLES, V32, P1487
  • [6] AN EFFICIENT AND CONVENIENT SYNTHESIS OF BRIDGED DELTA-LACTONES
    KIDO, F
    KAWADA, Y
    KATO, M
    YOSHIKOSHI, A
    [J]. TETRAHEDRON LETTERS, 1991, 32 (43) : 6159 - 6162
  • [7] SPIROANNULATION BY THE [2,3]SIGMATROPIC REARRANGEMENT VIA THE CYCLIC ALLYLSULFONIUM YLIDE - A STEREOSELECTIVE SYNTHESIS OF (+)-ACORENONE-B
    KIDO, F
    ABIKO, T
    KATO, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (02): : 229 - 233
  • [8] STEREOSELECTIVITY IN THE SIGMATROPIC REARRANGEMENT OF 8-MEMBERED AND 9-MEMBERED CYCLIC ALLYLSULFONIUM YLIDES - SYNTHESIS OF VINYL-SUBSTITUTED BUTYROLACTONES AND VALEROLACTONES
    KIDO, F
    SINHA, SC
    ABIKO, T
    WATANABE, M
    YOSHIKOSHI, A
    [J]. TETRAHEDRON, 1990, 46 (13-14) : 4887 - 4906
  • [9] A NOVEL SYNTHESIS OF ALLENIC LACTONES BY USE OF THE [2,3]SIGMATROPIC REARRANGEMENT OF CYCLIC PROPARGYLSULFONIUM YLIDES
    KIDO, F
    ABIKO, T
    KATO, M
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (09) : 2471 - 2474
  • [10] KIDO F, 1992, HETEROCYCLES, V33, P607