A total synthesis of (+)-Goniodiol using an anomeric oxygen-to-carbon rearrangement

被引:38
作者
Dixon, DJ [1 ]
Ley, SV [1 ]
Tate, EW [1 ]
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 19期
关键词
D O I
10.1039/a806584e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new route to (+)-Goniodiol 1, a potent and selective cytotoxin, is described, using a diastereoselective oxygen-to-carbon rearrangement of an anomerically linked silyl enol ether as the key step.
引用
收藏
页码:3125 / 3126
页数:2
相关论文
共 15 条
  • [1] PREPARATION OF 2-EXOMETHYLENE PENAM AND PENICILLIN-2-CARBOXYLATE SYSTEMS
    BALDWIN, JE
    FORREST, AK
    KO, S
    SHEPPARD, LN
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (02) : 81 - 83
  • [2] Buffet MF, 1997, SYNLETT, P1055
  • [3] BUFFET MF, IN PRESS SYNLETT
  • [4] DIXON DJ, IN PRESS SYNLETT
  • [5] 2 NEW STYRYL LACTONES, 9-DEOXYGONIOPYPYRONE AND 7-EPI-GONIOFUFURONE, FROM GONIOTHALAMUS-GIGANTEUS
    FANG, XP
    ANDERSON, JE
    CHANG, CJ
    MCLAUGHLIN, JL
    FANWICK, PE
    [J]. JOURNAL OF NATURAL PRODUCTS, 1991, 54 (04): : 1034 - 1043
  • [6] HUANG SL, 1978, SYNTHESIS-STUTTGART, P297
  • [7] ASYMMETRIC-SYNTHESIS AND BIOLOGICAL EVALUATION OF BETA-L-(2R,5S)-1,3-OXATHIOLANE AND ALPHA-L-(2R,5R)-1,3-OXATHIOLANE PYRIMIDINE AND PURINE NUCLEOSIDES AS POTENTIAL ANTI-HIV AGENTS
    JEONG, LS
    SCHINAZI, RF
    BEACH, JW
    KIM, HO
    NAMPALLI, S
    SHANMUGANATHAN, K
    ALVES, AJ
    MCMILLAN, A
    CHU, CK
    MATHIS, R
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (02) : 181 - 195
  • [8] LEY SV, 1994, SYNTHESIS-STUTTGART, P639
  • [9] Stereoselective syntheses of (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniodiol, (+)-9-deoxygoniopypyrone, (+)-altholactone, and (-)-goniofupyrone
    Mukai, C
    Hirai, S
    Hanaoka, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) : 6619 - 6626
  • [10] N-METHOXY-N-METHYLAMIDES AS EFFECTIVE ACYLATING AGENTS
    NAHM, S
    WEINREB, SM
    [J]. TETRAHEDRON LETTERS, 1981, 22 (39) : 3815 - 3818