ACID-CATALYZED CYCLIZATION OF CEMBRENE AND ISOCEMBROL

被引:19
作者
DAUBEN, WG [1 ]
HUBBELL, JP [1 ]
OBERHANSLI, P [1 ]
THIESSEN, WE [1 ]
机构
[1] OAK RIDGE NATL LAB,DIV CHEM,OAK RIDGE,TN 37830
关键词
D O I
10.1021/jo01319a001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The acid-catalyzed ring closure of cembrene, a 14-membered ring diterpene, and its derivatives has been studied. The predominant reaction pathway yields a hydrophenanthrene ring system. Under mild conditions isomeric tricyclic compounds are formed, but under more forcing conditions aromatization of a ring occurs. The detailed mechanisms of these reaction processes have been evaluated. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:669 / 673
页数:5
相关论文
共 24 条
  • [1] AUDIER HE, 1966, B SOC CHIM FR, P3181
  • [2] BOWDEN BF, 1977, TETRAHEDRON LETT, P3661
  • [3] CHEMISTRY OF EREMOPHILA SPP .8. CEMBRENETRIOL FROM EREMOPHILA-CLARKEI
    COATES, P
    GHISALBERTI, EL
    JEFFERIES, PR
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1977, 30 (12) : 2717 - 2721
  • [4] CEMBRENE, A 14-MEMBERED RING DITERPENE HYDROCARBON
    DAUBEN, WG
    THIESSEN, WE
    RESNICK, PR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (10) : 2015 - &
  • [5] THUJOPSENE REARRANGEMENTS - RING-SYSTEM VIA METHYL GROUP MIGRATION
    DAUBEN, WG
    FRIEDRIC.LE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (02) : 241 - &
  • [6] THUJOPSENE REARRANGEMENTS - RING-SYSTEM VIA RING CONTRACTION
    DAUBEN, WG
    AOYAGI, EI
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (02) : 251 - &
  • [7] CEMBRENE A 14-MEMBERED RING DITERPENE HYDROCARBON
    DAUBEN, WG
    THIESSEN, WE
    RESNICK, PR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (06) : 1693 - &
  • [8] SYNTHESIS OF (+ OR -)-CEMBRENE, A 14-MEMBERED RING DITERPENE
    DAUBEN, WG
    BEASLEY, GH
    BROADHURST, MD
    MULLER, B
    PEPPARD, DJ
    PESNELLE, P
    SUTER, C
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (17) : 4973 - 4980
  • [9] SYNTHESIS OF CEMBRENE - 14-MEMBERED RING DITERPENE
    DAUBEN, WG
    BEASLEY, GH
    BROADHURST, MD
    MULLER, B
    PEPPARD, DJ
    PESNELLE, P
    SUTER, C
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (14) : 4724 - 4726
  • [10] THUJOPSENE REARRANGEMENTS - CYCLOPROPYLCARBINYL SYSTEM
    DAUBEN, WG
    AOYAGI, EI
    FRIEDRIC.LE
    OBERHANS.P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (01) : 9 - &