PREPARATION OF (+)-TRICYCLO[6.2.1,0(2,7)]UNDEC-2(7)-EN-3-ONE AND ITS CONVERSION INTO (+)-EPI-BETA-SANTALENE

被引:7
作者
KAMIKUBO, T [1 ]
OGASAWARA, K [1 ]
机构
[1] TOHOKU UNIV, INST PHARMACEUT, SENDAI, MIYAGI 98077, JAPAN
关键词
D O I
10.1246/cl.1995.95
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Optically pure (+)-tricyclo[6.2.1.0(2,7)] undec-2(7)-en-3-one was first prepared from (+)-tricyclo[6.2.1.0(2,7)]undeca-4,9-dien-3-one in four steps. Conjugated addition occurred selectively from the methane-bridge side to give the 1,4-adduct which was converted into natural (+)-epi-beta-santalene.
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页码:95 / 96
页数:2
相关论文
共 19 条
  • [1] ARAI Y, 1988, B CHEM SOC JPN, V61, P476
  • [2] A NEW, STEREOSPECIFIC OLEFIN SYNTHESIS FROM 1,2-DIOLS
    COREY, EJ
    WINTER, RAE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (17) : 2677 - &
  • [3] EASTWOOD FW, 1970, TETRAHEDRON LETT, P5223
  • [4] STEREOSPECIFIC SYNTHETIC ROUTE TO CAMPHERENONE, CAMPHERENOL, EPICAMPHERENONE, BETA-SANTALENE, EPI-BETA-SANTALENE, YLANGOCAMPHOR, COPA-CAMPHOR, SATIVENE, AND COPACAMPHENE
    ECK, CR
    HODGSON, GL
    MACSWEEN.DF
    MILLS, RW
    MONEY, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (16): : 1938 - 1943
  • [5] EMDE H, 1982, SYNTHESIS-STUTTGART, P1
  • [6] FACILE, STEREOSPECIFIC PREPARATION OF OLEFINS FROM PINACOLS
    HIYAMA, T
    NOZAKI, H
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1973, 46 (07) : 2248 - 2249
  • [7] SYNTHESIS AND ABSOLUTE CONFIGURATION OF TERPENES (-)-CAMPHERENONE, (+)-EPICAMPHERENONE, (-)-BETA-SANTALENE, AND (+)-EPI-BETA-SANTALENE
    HODGSON, GL
    MACSWEENEY, DF
    MILLS, RW
    MONEY, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (07) : 235 - 236
  • [8] ME3SICL/HMPA ACCELERATED CONJUGATE ADDITION OF CATALYTIC COPPER REAGENT - STEREOSELECTIVE SYNTHESIS OF ENOL SILYL ETHER OF ALDEHYDE
    HORIGUCHI, Y
    MATSUZAWA, S
    NAKAMURA, E
    KUWAJIMA, I
    [J]. TETRAHEDRON LETTERS, 1986, 27 (34) : 4025 - 4028
  • [9] SYNTHESIS OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BY PALLADIUM(II)-CATALYZED DEHYDROSILYLATION OF SILYL ENOL ETHERS
    ITO, Y
    HIRAO, T
    SAEGUSA, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (05) : 1011 - 1013
  • [10] PI-FACIAL STEREOSELECTIVITIES IN DIELS-ALDER CYCLOADDITIONS TO A DISSYMMETRIC CYCLOHEXA-1,3-DIENE MOIETY IN A NOVEL, CAGED POLYCYCLIC FRAMEWORK
    MEHTA, G
    PADMA, S
    REDDY, SHK
    NETHAJI, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15): : 2049 - 2050