Carene terpenoids by gold-catalyzed cycloisomerization reactions

Chemical Communications

Volumn , Issue 22, 2004, Pages 2546-2547

  Fürstner, Alois ^a   Hannen, Peter ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; GOLD CHLORIDE; TERPENOID DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 9944255707     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b412354a     Document Type: Article

References (39)

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8. Reviews: M. P. Doyle, M. A. McKervey and T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley, New York, 1998; H. M. L. Davies, in Comprehensive Organic Synthesis, B. M. Trost and I. Fleming, eds., Pergamon, Oxford, 1991, vol. 4, p. 1031; A. Padwa and K. E. Krumpe, Tetrahedron, 1992, 48, 5385.
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10. R. M. Coates and R. M. Freidinger, Tetrahedron, 1970, 26, 3487; K. Mori and M. Matsui, Tetrahedron, 1970, 26, 2801; E. J. Corey and K. Achiwa, Tetrahedron Lett., 1969, 23, 1837; E. J. Corey and K. Achiwa, Tetrahedron Lett., 1969, 23, 3257; G. Büchi and J. D. White, J. Am. Chem. Soc., 1964, 86, 2884; F. Medina and A. Manjarrez, Tetrahedron, 1964, 20, 1807; see also: E. J. Corey, K. Achiwa and J. A. Katzenellenbogen, J. Am. Chem. Soc., 1969, 91, 4318; J. J. Plattner, U. T. Bhalerao and H. Rapoport, J. Am. Chem. Soc., 1969, 91, 4933.
11. R. M. Coates and R. M. Freidinger, Tetrahedron, 1970, 26, 3487; K. Mori and M. Matsui, Tetrahedron, 1970, 26, 2801; E. J. Corey and K. Achiwa, Tetrahedron Lett., 1969, 23, 1837; E. J. Corey and K. Achiwa, Tetrahedron Lett., 1969, 23, 3257; G. Büchi and J. D. White, J. Am. Chem. Soc., 1964, 86, 2884; F. Medina and A. Manjarrez, Tetrahedron, 1964, 20, 1807; see also: E. J. Corey, K. Achiwa and J. A. Katzenellenbogen, J. Am. Chem. Soc., 1969, 91, 4318; J. J. Plattner, U. T. Bhalerao and H. Rapoport, J. Am. Chem. Soc., 1969, 91, 4933.
12. R. M. Coates and R. M. Freidinger, Tetrahedron, 1970, 26, 3487; K. Mori and M. Matsui, Tetrahedron, 1970, 26, 2801; E. J. Corey and K. Achiwa, Tetrahedron Lett., 1969, 23, 1837; E. J. Corey and K. Achiwa, Tetrahedron Lett., 1969, 23, 3257; G. Büchi and J. D. White, J. Am. Chem. Soc., 1964, 86, 2884; F. Medina and A. Manjarrez, Tetrahedron, 1964, 20, 1807; see also: E. J. Corey, K. Achiwa and J. A. Katzenellenbogen, J. Am. Chem. Soc., 1969, 91, 4318; J. J. Plattner, U. T. Bhalerao and H. Rapoport, J. Am. Chem. Soc., 1969, 91, 4933.
13. R. M. Coates and R. M. Freidinger, Tetrahedron, 1970, 26, 3487; K. Mori and M. Matsui, Tetrahedron, 1970, 26, 2801; E. J. Corey and K. Achiwa, Tetrahedron Lett., 1969, 23, 1837; E. J. Corey and K. Achiwa, Tetrahedron Lett., 1969, 23, 3257; G. Büchi and J. D. White, J. Am. Chem. Soc., 1964, 86, 2884; F. Medina and A. Manjarrez, Tetrahedron, 1964, 20, 1807; see also: E. J. Corey, K. Achiwa and J. A. Katzenellenbogen, J. Am. Chem. Soc., 1969, 91, 4318; J. J. Plattner, U. T. Bhalerao and H. Rapoport, J. Am. Chem. Soc., 1969, 91, 4933.
14. R. M. Coates and R. M. Freidinger, Tetrahedron, 1970, 26, 3487; K. Mori and M. Matsui, Tetrahedron, 1970, 26, 2801; E. J. Corey and K. Achiwa, Tetrahedron Lett., 1969, 23, 1837; E. J. Corey and K. Achiwa, Tetrahedron Lett., 1969, 23, 3257; G. Büchi and J. D. White, J. Am. Chem. Soc., 1964, 86, 2884; F. Medina and A. Manjarrez, Tetrahedron, 1964, 20, 1807; see also: E. J. Corey, K. Achiwa and J. A. Katzenellenbogen, J. Am. Chem. Soc., 1969, 91, 4318; J. J. Plattner, U. T. Bhalerao and H. Rapoport, J. Am. Chem. Soc., 1969, 91, 4933.
15. R. M. Coates and R. M. Freidinger, Tetrahedron, 1970, 26, 3487; K. Mori and M. Matsui, Tetrahedron, 1970, 26, 2801; E. J. Corey and K. Achiwa, Tetrahedron Lett., 1969, 23, 1837; E. J. Corey and K. Achiwa, Tetrahedron Lett., 1969, 23, 3257; G. Büchi and J. D. White, J. Am. Chem. Soc., 1964, 86, 2884; F. Medina and A. Manjarrez, Tetrahedron, 1964, 20, 1807; see also: E. J. Corey, K. Achiwa and J. A. Katzenellenbogen, J. Am. Chem. Soc., 1969, 91, 4318; J. J. Plattner, U. T. Bhalerao and H. Rapoport, J. Am. Chem. Soc., 1969, 91, 4933.
16. R. M. Coates and R. M. Freidinger, Tetrahedron, 1970, 26, 3487; K. Mori and M. Matsui, Tetrahedron, 1970, 26, 2801; E. J. Corey and K. Achiwa, Tetrahedron Lett., 1969, 23, 1837; E. J. Corey and K. Achiwa, Tetrahedron Lett., 1969, 23, 3257; G. Büchi and J. D. White, J. Am. Chem. Soc., 1964, 86, 2884; F. Medina and A. Manjarrez, Tetrahedron, 1964, 20, 1807; see also: E. J. Corey, K. Achiwa and J. A. Katzenellenbogen, J. Am. Chem. Soc., 1969, 91, 4318; J. J. Plattner, U. T. Bhalerao and H. Rapoport, J. Am. Chem. Soc., 1969, 91, 4933.
17. α-Diazoketone cyclizations were pioneered by: G. Stork and J. Ficini, J. Am. Chem. Soc., 1961, 83, 4678.
18. Reviews: M. Méndez and A. M. Echavarren, Eur. J. Org. Chem., 2002, 15; G. C. Lloyd-Jones, Org. Biomol. Chem., 2003, 1, 215; C. Aubert, O. Buisine and M. Malacria, Chem. Rev., 2002, 102, 813; M. Méndez, V. Mamane and A. Fürstner, Chemtracts, 2003, 16, 397.
19. Reviews: M. Méndez and A. M. Echavarren, Eur. J. Org. Chem., 2002, 15; G. C. Lloyd-Jones, Org. Biomol. Chem., 2003, 1, 215; C. Aubert, O. Buisine and M. Malacria, Chem. Rev., 2002, 102, 813; M. Méndez, V. Mamane and A. Fürstner, Chemtracts, 2003, 16, 397.
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21. Reviews: M. Méndez and A. M. Echavarren, Eur. J. Org. Chem., 2002, 15; G. C. Lloyd-Jones, Org. Biomol. Chem., 2003, 1, 215; C. Aubert, O. Buisine and M. Malacria, Chem. Rev., 2002, 102, 813; M. Méndez, V. Mamane and A. Fürstner, Chemtracts, 2003, 16, 397.
22. For contributions from this laboratory, see: A. Fürstner, H. Szillat, B. Gabor and R. Mynott, J. Am. Chem. Soc., 1998, 120, 8305; A. Fürstner, H. Szillat and F. Stelzer, J. Am. Chem. Soc., 2000, 122, 6785; A. Fürstner, F. Stelzer and H. Szillat, J. Am. Chem. Soc., 2001, 123, 11 863; A. Fürstner and V. Mamane, J. Org. Chem., 2002, 67, 6264; A. Fürstner and V. Mamane, Chem. Commun., 2003, 2112; V. Mamane, P. Hannen and A. Fürstner, Chem. Eur. J., 2004, 10, 4556.
23. For contributions from this laboratory, see: A. Fürstner, H. Szillat, B. Gabor and R. Mynott, J. Am. Chem. Soc., 1998, 120, 8305; A. Fürstner, H. Szillat and F. Stelzer, J. Am. Chem. Soc., 2000, 122, 6785; A. Fürstner, F. Stelzer and H. Szillat, J. Am. Chem. Soc., 2001, 123, 11 863; A. Fürstner and V. Mamane, J. Org. Chem., 2002, 67, 6264; A. Fürstner and V. Mamane, Chem. Commun., 2003, 2112; V. Mamane, P. Hannen and A. Fürstner, Chem. Eur. J., 2004, 10, 4556.
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25. For contributions from this laboratory, see: A. Fürstner, H. Szillat, B. Gabor and R. Mynott, J. Am. Chem. Soc., 1998, 120, 8305; A. Fürstner, H. Szillat and F. Stelzer, J. Am. Chem. Soc., 2000, 122, 6785; A. Fürstner, F. Stelzer and H. Szillat, J. Am. Chem. Soc., 2001, 123, 11 863; A. Fürstner and V. Mamane, J. Org. Chem., 2002, 67, 6264; A. Fürstner and V. Mamane, Chem. Commun., 2003, 2112; V. Mamane, P. Hannen and A. Fürstner, Chem. Eur. J., 2004, 10, 4556.
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