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标题:Target-oriented multifunctional organocatalysis for enantioselective synthesis of bicyclo[3.3.1]nona-2,6-dien-9-ones. A formal asymmetric synthesis of huperzine A
时间:2019-03-15 00:14:21
DOI:10.1016/j.tet.2012.05.061
作者:Xiao-Hua Ding;Xiang Li;Dan Liu;Wei-Chen Cui;Xuan Ju
出版源: 《Tetrahedron》 ,2012 ,68 (31) :6240---6248
摘要:Target-oriented multifunctional organocatalysis for enantioselective synthesis of bicyclo[3.3.1]nona-2,6-dien-9-ones. A formal asymmetric synthesis of huperzine A(−)-Huperzine AMultifunctional organocatalysisMichael additionEnantioselectivityTarget-oriented methodologyA target-oriented highly enantioselective multifunctional organocatalytic approach has been developed to construct the ...
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目录:
  • Target-oriented multifunctional organocatalysis for enantioselective synthesis of bicyclo[3.3.1]nona-2,6-dien-9-ones. A for ...
    • 1. Introduction
    • 2. Results and discussion
    • 3. Summary
    • 4. Experimental section
      • 4.1. General
      • 4.2. Preparation of catalysts 3–7
        • 4.2.1. 1-((1R,2R)-2-Aminocyclohexyl)-3-(2(dimethylamino)ethyl) thiourea (3)
        • 4.2.2. 1-((1R,2R)-2-Aminocyclohexyl)-3-((S)-1-(dimethylamino)-3-methylbutan-2-yl)thiourea (4)
        • 4.2.3. 1-((1R,2R)-2-Aminocyclohexyl)-3-((S)-2-(dimethylamino)-3-methylbutyl)thiourea (5)
        • 4.2.4. 1-((1R,2R)-2-Aminocyclohexyl)-3-((1S,2S)-2-(dimethyl amino) cyclohexyl) thiourea (6)
        • 4.2.5. 1-((1R,2R)-2-Aminocyclohexyl)-3-((1R,2R)-2-(dimethyl amino) cyclohexyl)thiourea (7)
      • 4.3. Preparation of β-ketoesters 10b, 10d, 10e, and 10f
        • 4.3.1. Ethyl 6-hydroxy-2-methoxy-7,8-dihydroquinoline-5-carboxylate (10b)
        • 4.3.2. Methyl 2-ethoxy-6-hydroxy-7,8-dihydroquinoline-5-carboxylate (10d)
        • 4.3.3. Methyl 6-hydroxy-2-isopropoxy-7,8-dihydroquinoline-5-carboxylate (10e)
        • 4.3.4. Ethyl 2-ethoxy-6-hydroxy-7,8-dihydroquinoline-5-carboxylate (10f)
      • 4.4. Preparation of β-ketoesters 14b, 14c, 14d, 14e, 14f, and 14g
        • 4.4.1. Methyl 2-hydroxy-5-methyl-3,4-dihydronaphthalene-1-carbo xylate (14b)
        • 4.4.2. Methyl 2-hydroxy-5-methoxy-3,4-dihydronaphthalene-1-carbo xylate (14c)
        • 4.4.3. Methyl 2-hydroxy-6-methoxy-3,4-dihydronaphthalene-1-carboxylate (14d)
        • 4.4.4. Methyl 6-bromo-2-hydroxy-3,4-dihydronaphthalene-1-carboxylate (14e)
        • 4.4.5. Methyl 2-hydroxy-7-methoxy-3,4-dihydronaphthalene-1-carboxylate (14f)
        • 4.4.6. Methyl 2-hydroxy-7-methyl-3,4-dihydronaphthalene-1-carboxylate (14g)
      • 4.5. The tandem Michael–aldol reaction
        • 4.5.1. (5S,9R)-Methyl 2-methoxy-7-methyl-11-oxo-5,6,9,10-tetrahydro-5,9-methano-cycloocta[b]pyridine-5-carboxylate (13a)
        • 4.5.2. (5S,9R)-Ethyl 2-methoxy-7-methyl-11-oxo-5,6,9,10-tetrahydro-5,9-methano-cycloocta[b]pyridine-5-carboxylate (13b)
        • 4.5.3. (5S,9R)-Benzyl 2-methoxy-7-methyl-11-oxo-5,6,9,10-tetrahydro- 5,9-methano-cycloocta[b]pyridine-5-carboxylate (13c)
        • 4.5.4. (5S,9R)-Methyl 2-ethoxy-7-methyl-11-oxo-5,6,9,10-tetra hydro-5,9-methano-cycloocta[b]pyridine-5-carboxylate (13d)
        • 4.5.5. (5S,9R)-Methyl 2-isopropoxy-7-methyl-11-oxo-5,6,9,10-tetra- hydro-5,9-methano-cycloocta[b]pyridine-5-carboxylate (13e)
        • 4.5.6. (5S,9R)-Ethyl 2-ethoxy-7-methyl-11-oxo-5,6,9,10-tetrahydro-5,9-methano-cycloocta[b]pyridine-5-carboxylate (13f)
        • 4.5.7. (5S,9R)-Methyl 7-methyl-11-oxo-5,6,9,10-tetrahydro-5,9-methanobenzo-[8]annulene-5-carboxylate (16a)
        • 4.5.8. (5S,9R)-Methyl 1,7-dimethyl-11-oxo-5,6,9,10-tetrahydro-5,9-methanobenzo-[8]annulene-5-carboxylate (16b)
        • 4.5.9. (5S,9R)-Methyl 1-methoxy-7-methyl-11-oxo-5,6,9,10-tetrah- ydro-5,9-methanobenzo[8]annulene-5-carboxylate (16c)
        • 4.5.10. (5S,9R)-Methyl 2-methoxy-7-methyl-11-oxo-5,6,9,10-tetra hydro-5,9-methano-benzo[8]annulene-5-carboxylate (16d)
        • 4.5.11. (5S,9R)-Methyl 3,7-dimethyl-11-oxo-5,6,9,10-tetrahydro-5,9-methanobenzo-[8]annulene-5-carboxylate (16e)
        • 4.5.12. (5S,9R)-Methyl 3-methoxy-7-methyl-11-oxo-5,6,9,10-tetra hydro-5,9-methano-benzo[8]annulene-5-carboxylate (16f)
        • 4.5.13. (5S,9R)-Methyl 3,7-dimethyl-11-oxo-5,6,9,10-tetrahydro-5,9-methanobenzo-[8]annulene-5-carboxylate (16g)
        • 4.5.14. (5S,9R)-Methyl 2-methoxy-11-oxo-5,6,9,10-tetrahydro-5,9-methanocyclo-octa[b]pyridine-5-carboxylate (18a)
        • 4.5.15. (5S,9R)-methyl 2-methoxy-11-oxo-7-propyl-5,6,9,10-tetrahydro-5,9-methano-cycloocta[b]pyridine-5-carboxylate (18b)
        • 4.5.16. (5S,9R)-Methyl 7-isopropyl-2-methoxy-11-oxo-5,6,9,10-tetra- hydro-5,9-methano-cycloocta[b]pyridine-5-carboxylate (18c)
    • Acknowledgements
    • Supplementary data
    • References and notes

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