Three-carbon ring expansion by cyclopropane insertion: Macrocyclic musks from readily available C-12 starting materials

Organic Letters

Volumn 6, Issue 17, 2004, Pages 2989-2991

  Rüedi, Georg ^a   Nagel, Matthias ^a,b   Hansen, Hans Jürgen ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b SWISS FEDERAL LABORATORIES FOR MATERIALS SCIENCE AND TECHNOLOGY   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CYCLOPROPANE DERIVATIVE; MACROCYCLIC COMPOUND; METHYL GROUP; MUSK;

ARTICLE; CHEMICAL BOND; GEOMETRY; PYROLYSIS; REACTION ANALYSIS; SUBSTITUTION REACTION; THERMAL ANALYSIS;

EID: 4444333770     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0487027     Document Type: Article

References (45)

1. For leading references on musk odorants, see: (a) Fráter, G.; Bajgrowicz, J. A.; Kraft, P. Tetrahedron 1998, 54, 7633. (b) Williams, A. S. Synthesis 1999, 1707. (c) Fráter, G.; Bajgrowicz, J. A.; Denis, C.; Kraft, P. Angew. Chem., Int. Ed. 2000, 39, 2980. (d) Fráter, G.; Lamparsky, D. In Perfumes: Art, Science and Technology; Müller, P. M., Lamparsky, D., Eds.; Elsevier: London, New York, 1991; Chapter 20, pp 533-555. (e) Ohloff, G. Riechstoffe und Geruchssinn. Die Molekulare Welt der Düfte; Springer: Berlin, 1990; Chapter 9, pp 195-219. (f) Mookherjee, B. D.; Wilson, R. A. In Fragrance Chemistry: The Science of the Sense of Smell; Theimer, E. T., Ed.; Academic Press: New York, 1982; Chapter 12, pp 433-494.
2. For leading references on musk odorants, see: (a) Fráter, G.; Bajgrowicz, J. A.; Kraft, P. Tetrahedron 1998, 54, 7633. (b) Williams, A. S. Synthesis 1999, 1707. (c) Fráter, G.; Bajgrowicz, J. A.; Denis, C.; Kraft, P. Angew. Chem., Int. Ed. 2000, 39, 2980. (d) Fráter, G.; Lamparsky, D. In Perfumes: Art, Science and Technology; Müller, P. M., Lamparsky, D., Eds.; Elsevier: London, New York, 1991; Chapter 20, pp 533-555. (e) Ohloff, G. Riechstoffe und Geruchssinn. Die Molekulare Welt der Düfte; Springer: Berlin, 1990; Chapter 9, pp 195-219. (f) Mookherjee, B. D.; Wilson, R. A. In Fragrance Chemistry: The Science of the Sense of Smell; Theimer, E. T., Ed.; Academic Press: New York, 1982; Chapter 12, pp 433-494.
3. For leading references on musk odorants, see: (a) Fráter, G.; Bajgrowicz, J. A.; Kraft, P. Tetrahedron 1998, 54, 7633. (b) Williams, A. S. Synthesis 1999, 1707. (c) Fráter, G.; Bajgrowicz, J. A.; Denis, C.; Kraft, P. Angew. Chem., Int. Ed. 2000, 39, 2980. (d) Fráter, G.; Lamparsky, D. In Perfumes: Art, Science and Technology; Müller, P. M., Lamparsky, D., Eds.; Elsevier: London, New York, 1991; Chapter 20, pp 533-555. (e) Ohloff, G. Riechstoffe und Geruchssinn. Die Molekulare Welt der Düfte; Springer: Berlin, 1990; Chapter 9, pp 195-219. (f) Mookherjee, B. D.; Wilson, R. A. In Fragrance Chemistry: The Science of the Sense of Smell; Theimer, E. T., Ed.; Academic Press: New York, 1982; Chapter 12, pp 433-494.
4. For leading references on musk odorants, see: (a) Fráter, G.; Bajgrowicz, J. A.; Kraft, P. Tetrahedron 1998, 54, 7633. (b) Williams, A. S. Synthesis 1999, 1707. (c) Fráter, G.; Bajgrowicz, J. A.; Denis, C.; Kraft, P. Angew. Chem., Int. Ed. 2000, 39, 2980. (d) Fráter, G.; Lamparsky, D. In Perfumes: Art, Science and Technology; Müller, P. M., Lamparsky, D., Eds.; Elsevier: London, New York, 1991; Chapter 20, pp 533-555. (e) Ohloff, G. Riechstoffe und Geruchssinn. Die Molekulare Welt der Düfte; Springer: Berlin, 1990; Chapter 9, pp 195-219. (f) Mookherjee, B. D.; Wilson, R. A. In Fragrance Chemistry: The Science of the Sense of Smell; Theimer, E. T., Ed.; Academic Press: New York, 1982; Chapter 12, pp 433-494.
5. For leading references on musk odorants, see: (a) Fráter, G.; Bajgrowicz, J. A.; Kraft, P. Tetrahedron 1998, 54, 7633. (b) Williams, A. S. Synthesis 1999, 1707. (c) Fráter, G.; Bajgrowicz, J. A.; Denis, C.; Kraft, P. Angew. Chem., Int. Ed. 2000, 39, 2980. (d) Fráter, G.; Lamparsky, D. In Perfumes: Art, Science and Technology; Müller, P. M., Lamparsky, D., Eds.; Elsevier: London, New York, 1991; Chapter 20, pp 533-555. (e) Ohloff, G. Riechstoffe und Geruchssinn. Die Molekulare Welt der Düfte; Springer: Berlin, 1990; Chapter 9, pp 195-219. (f) Mookherjee, B. D.; Wilson, R. A. In Fragrance Chemistry: The Science of the Sense of Smell; Theimer, E. T., Ed.; Academic Press: New York, 1982; Chapter 12, pp 433-494.
6. For leading references on musk odorants, see: (a) Fráter, G.; Bajgrowicz, J. A.; Kraft, P. Tetrahedron 1998, 54, 7633. (b) Williams, A. S. Synthesis 1999, 1707. (c) Fráter, G.; Bajgrowicz, J. A.; Denis, C.; Kraft, P. Angew. Chem., Int. Ed. 2000, 39, 2980. (d) Fráter, G.; Lamparsky, D. In Perfumes: Art, Science and Technology; Müller, P. M., Lamparsky, D., Eds.; Elsevier: London, New York, 1991; Chapter 20, pp 533-555. (e) Ohloff, G. Riechstoffe und Geruchssinn. Die Molekulare Welt der Düfte; Springer: Berlin, 1990; Chapter 9, pp 195-219. (f) Mookherjee, B. D.; Wilson, R. A. In Fragrance Chemistry: The Science of the Sense of Smell; Theimer, E. T., Ed.; Academic Press: New York, 1982; Chapter 12, pp 433-494.
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