A new chemoenzymatic Baylis-Hillman approach for the synthesis of enantiomerically enriched umbelactones

被引:25
作者
Kamal, Ahmed [1 ]
Krishnaji, Tadiparthi [1 ]
Reddy, P. Venkat [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem, Biotransformat Lab, Hyderabad 500007, Andhra Pradesh, India
关键词
Baylis-hillmati; lipase-resolution; ring-closing metathesis;
D O I
10.1016/j.tetlet.2007.07.139
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and convenient strategy for the enantioselective synthesis of enantiomerically enriched umbelactones is described utilizing a lipase-mediated resolution protocol, Baylis-Hillman reaction and ring closing metathesis as key steps. The lipase-resolution is carried out using several lipases from various sources in different solvents to afford the required intermediate 8 in good yield and high enantioselectivity. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7232 / 7235
页数:4
相关论文
共 27 条
  • [11] PHOTOOXYGENATION OF 1-VINYLCYCLOALKENES - THE COMPETITION BETWEEN ENE REACTION AND CYCLO-ADDITION OF SINGLET OXYGEN
    HERZ, W
    JUO, RR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (05) : 618 - 627
  • [12] BASICITY OF, SN2 REACTIVITY OF, AND BASIC CATALYSIS BY 1-AZABICYCLO[2.2.1]HEPTANE
    HINE, J
    CHEN, YJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10) : 2091 - 2094
  • [13] Hiroshi H., 1989, J ORG CHEM, V54, P1346
  • [14] Huawei L., 2005, CHINESE CHEM LETT, V16, P716
  • [15] Lipase-catalysed resolution of N-(3-cyano-2-hydroxy propan-1-yl)phthalimide -: Synthesis of (R)-GABOB and (R)-carnitine
    Kamal, Ahmed
    Krishnaji, Tadiparthi
    Khan, M. Naseer A.
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2007, 47 (1-2) : 1 - 5
  • [16] Chemoenzymatic synthesis of enantiomerically enriched kavalactones
    Kamal, Ahmed
    Krishnaji, Tadiparthi
    Khanna, G. B. Ramesh
    [J]. TETRAHEDRON LETTERS, 2006, 47 (49) : 8657 - 8660
  • [17] Lee G.C.M., 1991, PCT Int. Appl. WO 91 16,055, Patent No. [91 16,055, 9116055]
  • [18] A new approach for the asymmetric total synthesis of umbelactone
    Liu, HW
    Zhang, T
    Li, YL
    [J]. CHIRALITY, 2006, 18 (04) : 223 - 226
  • [19] SYNTHESIS OF THE ENANTIOMERS OF UMBELACTONE - CONFIGURATIONAL ASSIGNMENT OF THE NATURAL PRODUCT
    ORTUNO, RM
    BIGORRA, J
    FONT, J
    [J]. TETRAHEDRON, 1987, 43 (09) : 2199 - 2202
  • [20] Otsuka H, 1998, CHEM PHARM BULL, V46, P1180