NEW ROUTE TO (-)-FRONTALIN AND (-)-MALYNGOLIDE VIA EPOXYKETONE REARRANGEMENT

被引:32
作者
ASAOKA, M
HAYASHIBE, S
SONODA, S
TAKEI, H
机构
[1] Department of Life Chemistry, Tokyo Institute of Technology, Midoriku, Yokohama
关键词
(-)-FRONTALINE; (-)-MALYNGOLIDE; RING CONTRACTION; EPOXYKETONE; REARRANGEMENT;
D O I
10.1016/S0040-4020(01)96151-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of the title compounds by utilizing BF3.Et2O catalyzed ring contraction of 2,3-epoxycyclohexanones leading to 2-alkyl-2-formylcyclopentanones is described.
引用
收藏
页码:6967 / 6974
页数:8
相关论文
共 16 条
  • [1] CONSTRUCTION OF CHIRAL QUARTERNARY CARBON CENTERS USING 3-SUBSTITUTED 5-TRIMETHYLSILYL-2-CYCLOHEXENONES - SYNTHESIS OF (+)-ALPHA-CUPARENONE
    ASAOKA, M
    TAKENOUCHI, K
    TAKEI, H
    [J]. TETRAHEDRON LETTERS, 1988, 29 (03) : 325 - 328
  • [2] DIASTEREOSELECTIVE 1,4-ADDITION OF VARIOUS NUCLEOPHILES TO 5-TRIMETHYLSILYL-2-CYCLOHEXENONE - SYNTHESIS OF (+)-RAMULOSIN
    ASAOKA, M
    SONODA, S
    FUJII, N
    TAKEI, H
    [J]. TETRAHEDRON, 1990, 46 (05) : 1541 - 1552
  • [3] HO TL, 1988, CARBOCYCLE CONSTRUCT, P579
  • [4] AN ENANTIOCONTROLLED SYNTHESIS OF (-)-MALYNGOLIDE
    HONDA, T
    IMAI, M
    KEINO, K
    TSUBUKI, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (10): : 2677 - 2680
  • [5] NEW ASPECTS OF OXYPALLADATION OF ALKENES
    HOSOKAWA, T
    MURAHASHI, SI
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (02) : 49 - 54
  • [6] STEREOSELECTIVE SYNTHESIS OF MARINE ANTIBIOTIC (-)-MALYNGOLIDE AND ITS STEREOISOMERS
    ICHIMOTO, I
    MACHIYA, K
    KIRIHATA, M
    UEDA, H
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (03): : 657 - 662
  • [7] ON THE STEREOCHEMISTRY OF THE BF3-CATALYZED REARRANGEMENT OF (+)-ISOPHORONE OXIDE
    KUNISCH, F
    HOBERT, K
    WELZEL, P
    [J]. TETRAHEDRON LETTERS, 1985, 26 (49) : 6039 - 6042
  • [8] MATSUO K, 1981, CHEM PHARM BULL, V29, P3047
  • [9] SYNTHESIS OF OPTICALLY-ACTIVE PHEROMONES
    MORI, K
    [J]. TETRAHEDRON, 1989, 45 (11) : 3233 - 3298
  • [10] OHOTA H, 1989, TETRAHEDRON, V45, P5469