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Volumn 5, Issue 8, 2003, Pages 1301-1303

Synthesis of a tricyclic mescaline analogue by catalytic C-H bond activation

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; MESCALINE; TRICYCLIC ANTIDEPRESSANT AGENT; DRUG DERIVATIVE; GALLIC ACID; GALLIC ACID METHYL ESTER; RUTHENIUM;

EID: 0038601661     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034228d     Document Type: Article
Times cited : (89)

References (27)
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    • note
    • 3H]-mesulergine.
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    • For examples of the application of C-H bond activation in target-oriented synthesis, see: (a) Harris, P. W. R.; Woodgate. P. D. J. Organomet. Chem. 1997, 530, 211. (b) Johnson, J. A.; Sames, D. J. Am. Chem. Soc. 2000, 122, 6321. (c) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856. (d) Wehn, P. M.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 12950.
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    • Harris, P.W.R.1    Woodgate, P.D.2
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    • For examples of the application of C-H bond activation in target-oriented synthesis, see: (a) Harris, P. W. R.; Woodgate. P. D. J. Organomet. Chem. 1997, 530, 211. (b) Johnson, J. A.; Sames, D. J. Am. Chem. Soc. 2000, 122, 6321. (c) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856. (d) Wehn, P. M.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 12950.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 6321
    • Johnson, J.A.1    Sames, D.2
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    • For examples of the application of C-H bond activation in target-oriented synthesis, see: (a) Harris, P. W. R.; Woodgate. P. D. J. Organomet. Chem. 1997, 530, 211. (b) Johnson, J. A.; Sames, D. J. Am. Chem. Soc. 2000, 122, 6321. (c) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856. (d) Wehn, P. M.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 12950.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 11856
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    • For examples of the application of C-H bond activation in target-oriented synthesis, see: (a) Harris, P. W. R.; Woodgate. P. D. J. Organomet. Chem. 1997, 530, 211. (b) Johnson, J. A.; Sames, D. J. Am. Chem. Soc. 2000, 122, 6321. (c) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856. (d) Wehn, P. M.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 12950.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 12950
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    • For examples of the application of rhodium-carbenoid insertions into C-H bonds in target-oriented synthesis, see: (a) Taber, D.; Song, Y. J. Org. Chem. 1997, 62, 6603. (b) Davies, H. M. L.; Stafford, D. G.; Hansen, T. Org. Lett. 1999, 1, 233. (c) Davies, H. M. L.; Gregg, T. M. Tetrahedron Lett. 2002, 43, 4951 and references therein.
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    • For examples of the application of rhodium-carbenoid insertions into C-H bonds in target-oriented synthesis, see: (a) Taber, D.; Song, Y. J. Org. Chem. 1997, 62, 6603. (b) Davies, H. M. L.; Stafford, D. G.; Hansen, T. Org. Lett. 1999, 1, 233. (c) Davies, H. M. L.; Gregg, T. M. Tetrahedron Lett. 2002, 43, 4951 and references therein.
    • (1999) Org. Lett. , vol.1 , pp. 233
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  • 19
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    • and references therein
    • For examples of the application of rhodium-carbenoid insertions into C-H bonds in target-oriented synthesis, see: (a) Taber, D.; Song, Y. J. Org. Chem. 1997, 62, 6603. (b) Davies, H. M. L.; Stafford, D. G.; Hansen, T. Org. Lett. 1999, 1, 233. (c) Davies, H. M. L.; Gregg, T. M. Tetrahedron Lett. 2002, 43, 4951 and references therein.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4951
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  • 21
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    • 4-Methoxy-3,5-bis-hydroxy-benzoic acid methyl ester is prepared by alkylation of commercially available methyl benzoate. Cardona, M. L.; Fernandez, M. I.; Garcia, M. B.; Pedro, J. R. Tetrahedron 1986, 42, 2725.
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    • note
    • 2 resulted in reduced product yield (60% NMR yield).
  • 27
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    • note
    • No starting material or side products were isolated after silica gel chromatography. The remaining material is attributed to intractable mixtures of oligomers or polymers. Lowering the concentration of the reaction improved the product yield.


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