Enantioselective synthesis of cadinanes starting from R-(-)-or S-(+)-carvone

被引:10
|
作者
Baranovsky, AV
Jansen, BJM
Meulemans, TM
de Groot, A
机构
[1] Agr Univ Wageningen, Organ Chem Lab, NL-6703 HB Wageningen, Netherlands
[2] Byelarussian Acad Sci, Inst Bioorgan Chem, Lab Steroid Chem, Minsk 220141, BELARUS
关键词
D O I
10.1016/S0040-4020(98)00234-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new enantioselective synthesis of cadinanes, using the Mukaiyama-Michael reaction, was developed starting from R-(-)- or S-(+)-carvone. This approach gives an easy and direct access to the cadinane skeleton and the scope proved to be complementary to a formylation-annelation sequence. The applicability of the method was demonstrated by the enantioselective synthesis of 1,9-cadinadien-3-one and 4-methoxy-1,9-cadinadien-3-one. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5623 / 5634
页数:12
相关论文
共 50 条
  • [1] Enantioselective synthesis of R-(-)-ligularenolide starting from S-(+)-carvone
    Jenniskens, LHD
    deGroot, A
    TETRAHEDRON LETTERS, 1997, 38 (42) : 7463 - 7464
  • [2] Enantioselective synthesis of R-(-)-ligularenolide starting from S-(+)-carvone
    Jenniskens, L. H. D.
    De Groot, A.
    Tetrahedron Letters, 38 (42):
  • [3] Enantioselective synthesis of R-(-)-ligularenolide and the progesterone receptor ligand R-(-)-PF1092C starting from S-(+)-carvone
    Jenniskens, LHD
    de Groot, A
    TETRAHEDRON, 1998, 54 (21) : 5617 - 5622
  • [4] Enantioselective synthesis of highly functionalised cyclohexanones starting from R-(-)-carvone
    Meulemans, TM
    Stork, GA
    Jansen, BJM
    de Groot, A
    TETRAHEDRON LETTERS, 1998, 39 (36) : 6565 - 6568
  • [5] Enantioselective synthesis of R-(+)-α and S-(-)-α-lipoic acid
    Chavan, SP
    Praveen, C
    Ramakrishna, G
    Kalkote, UR
    TETRAHEDRON LETTERS, 2004, 45 (31) : 6027 - 6028
  • [6] The enantioselective synthesis of key intermediates for the synthesis of (+)-brevifloralactone from R-(-)-carvone
    Olkhovik, V
    Masalov, N
    Jansen, BJM
    de Groot, A
    TETRAHEDRON LETTERS, 2001, 42 (29) : 4903 - 4905
  • [7] ENANTIOSELECTIVE SYNTHESIS OF R-(-)-CRYPTOSTYLINE AND S-(+)-CRYPTOSTYLINE-II
    CZARNOCKI, Z
    MIECZKOWSKI, JB
    POLISH JOURNAL OF CHEMISTRY, 1995, 69 (10) : 1447 - 1450
  • [8] R-(+)- and S-(-)-Carvone:: influence of chirality on locomotion activity in mice
    Buchbauer, G
    Jäger, W
    Gruber, A
    Dietrich, H
    FLAVOUR AND FRAGRANCE JOURNAL, 2005, 20 (06) : 686 - 689
  • [9] ENANTIOSELECTIVE DISPOSITION OF R-(-)-PRENYLAMINE AND S-(+)-PRENYLAMINE IN THE RAT
    GIETL, Y
    SPAHN, H
    MUTSCHLER, E
    ARZNEIMITTEL-FORSCHUNG/DRUG RESEARCH, 1989, 39-2 (08): : 853 - 856
  • [10] Enantioselective synthesis of functionalised decalones by Robinson annulation of substituted cyclohexanones, derived from R-(-)-carvone
    Jansen, BJM
    Hendrikx, CCJ
    Masalov, N
    Stork, GA
    Meulemans, TM
    Macaev, FZ
    de Groot, A
    TETRAHEDRON, 2000, 56 (14) : 2075 - 2094