TOTAL SYNTHESIS OF (+-)-PATCHOULI ALCOHOL AND (+-)-SEYCHELLENE VIA A COMMON HOMOISOTWISTANE INTERMEDIATE

被引:43
作者
YAMADA, K
KYOTANI, Y
MANABE, S
SUZUKI, M
机构
[1] Department of Chemistry, Faculty of Science, Nagoya University, Chikusa, Nagoya
关键词
D O I
10.1016/0040-4020(79)80064-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Base-catalyzed cyclization of a conjugated cyclohexenone derivative 16 afforded in a single step a homoisotwistane derivative 17, which was converted to a ketone 22. Both (±)-patchouli alcohol 1 and (±)-seychellene 2 were synthesized using reactions at the bridgehead position (C-7) of a bicyclo[3.3.1]nonan-2-one system contained in 22. © 1979.
引用
收藏
页码:293 / 298
页数:6
相关论文
共 37 条
  • [1] TERPENES .14. SYNTHESIS OF PATCHOULI ALCOHOL
    BUCHI, G
    MACLEOD, WD
    PADILLA, JO
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (20) : 4438 - &
  • [2] BURGER U, 1970, TETRAHEDRON LETT, P3057
  • [3] CHAKRAVARTI D, 1965, J INDIAN CHEM SOC, V42, P607
  • [4] COREY EJ, 1975, TETRAHEDRON LETT, P2647
  • [5] DANISHEFSKY S, 1968, J CHEM SOC CHEM COMM, P1287
  • [6] DOBLER M, 1963, P CHEM SOC LONDON, P383
  • [7] SYNTHESIS OF (+/-) SEYCHELLENE
    FRATER, G
    [J]. HELVETICA CHIMICA ACTA, 1974, 57 (01) : 172 - 179
  • [8] CARBENOID SPECIES FROM METHYL AND METHYLENE HALIDES
    FRIEDMAN, L
    HONOUR, RJ
    BERGER, JG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (15) : 4640 - &
  • [9] DEHYDROBROMINATION OF "3-BROMOTRICYCLO[5.3.1.03,8]UNDECANE (3-BROMO-4-HOMOISOTWISTANE) AND SOME ADDITION-REACTIONS OF TRICYCLO[5.3.1.03,8]-UNDEC-2-ENE - STEREOCHEMISTRY OF FORMATION AND REACTION OF AN ANTI-BREDT COMPOUND PROBED BY DEUTERIUM SUBSTITUTION
    FUJIKURA, Y
    INAMOTO, Y
    TAKAISHI, N
    IKEDA, H
    AIGAMI, K
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (20): : 2133 - 2137
  • [10] TOTAL SYNTHESIS OF (+/-)-SEYCHELLENE
    FUKAMIYA, N
    KATO, M
    YOSHIKOSHI, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (17): : 1843 - 1847