Synthesis of enantiomerically pure 7-oxabicyclo[2.2.1]hept-2-enes precursors in the preparation of taxol analogues

Tetrahedron Asymmetry

Volumn 7, Issue 11, 1996, Pages 3163-3168

  Theurillat Moritz, Viviane ^a   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

NORBORNANE DERIVATIVE; TAXANE DERIVATIVE;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030575846     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00418-1     Document Type: Article

References (19)

1. 1. Yadav, J. S.; Renduchintala, R.; Samala, L. Tetrahedron Lett. 1994, 35, 3617.
2. 2. Guidi, A.; Theurillat-Moritz, V.; Vogel, P.; Pinkerton, A. A. Tetrahedron:Asymmetry 1996, 7
3. 3. For a review on the synthesis of enantiomerically pure 7-oxabicyclo[2.2.1]heptanes, see ref. 1, 3-12 in ref. 2.
4. 4. Harada, N.; Nakanishi, K. in "Circular Dichroïc Spectroscopy - Exciton Coupling in Organic Stereochemistry"; Ed. University Science Books and Oxford University Press, Oxford, 1983.
5. 5. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S., Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C. H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1977, 45, 326; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Lightner, D. A. in "Analytical Applications of Circular Dichroism", Purdie, N.; Brittain, H. G. Eds., Elsevier, Amsterdam 1994, p. 131; "Circular Dichroism, Principles and Applications", Nakanishi, K.; Berova, N.; Woody, R. W.; Eds., VCH Publishers, New York, 1994.
6. 5. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S., Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C. H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1977, 45, 326; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Lightner, D. A. in "Analytical Applications of Circular Dichroism", Purdie, N.; Brittain, H. G. Eds., Elsevier, Amsterdam 1994, p. 131; "Circular Dichroism, Principles and Applications", Nakanishi, K.; Berova, N.; Woody, R. W.; Eds., VCH Publishers, New York, 1994.
7. 5. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S., Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C. H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1977, 45, 326; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Lightner, D. A. in "Analytical Applications of Circular Dichroism", Purdie, N.; Brittain, H. G. Eds., Elsevier, Amsterdam 1994, p. 131; "Circular Dichroism, Principles and Applications", Nakanishi, K.; Berova, N.; Woody, R. W.; Eds., VCH Publishers, New York, 1994.
8. 5. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S., Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C. H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1977, 45, 326; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Lightner, D. A. in "Analytical Applications of Circular Dichroism", Purdie, N.; Brittain, H. G. Eds., Elsevier, Amsterdam 1994, p. 131; "Circular Dichroism, Principles and Applications", Nakanishi, K.; Berova, N.; Woody, R. W.; Eds., VCH Publishers, New York, 1994.
9. 5. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S., Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C. H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1977, 45, 326; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Lightner, D. A. in "Analytical Applications of Circular Dichroism", Purdie, N.; Brittain, H. G. Eds., Elsevier, Amsterdam 1994, p. 131; "Circular Dichroism, Principles and Applications", Nakanishi, K.; Berova, N.; Woody, R. W.; Eds., VCH Publishers, New York, 1994.
10. 5. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S., Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C. H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1977, 45, 326; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Lightner, D. A. in "Analytical Applications of Circular Dichroism", Purdie, N.; Brittain, H. G. Eds., Elsevier, Amsterdam 1994, p. 131; "Circular Dichroism, Principles and Applications", Nakanishi, K.; Berova, N.; Woody, R. W.; Eds., VCH Publishers, New York, 1994.
11. 5. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S., Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C. H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1977, 45, 326; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Lightner, D. A. in "Analytical Applications of Circular Dichroism", Purdie, N.; Brittain, H. G. Eds., Elsevier, Amsterdam 1994, p. 131; "Circular Dichroism, Principles and Applications", Nakanishi, K.; Berova, N.; Woody, R. W.; Eds., VCH Publishers, New York, 1994.
12. 5. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S., Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C. H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1977, 45, 326; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Lightner, D. A. in "Analytical Applications of Circular Dichroism", Purdie, N.; Brittain, H. G. Eds., Elsevier, Amsterdam 1994, p. 131; "Circular Dichroism, Principles and Applications", Nakanishi, K.; Berova, N.; Woody, R. W.; Eds., VCH Publishers, New York, 1994.
13. 5. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S., Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C. H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1977, 45, 326; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Lightner, D. A. in "Analytical Applications of Circular Dichroism", Purdie, N.; Brittain, H. G. Eds., Elsevier, Amsterdam 1994, p. 131; "Circular Dichroism, Principles and Applications", Nakanishi, K.; Berova, N.; Woody, R. W.; Eds., VCH Publishers, New York, 1994.
14. 5. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S., Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C. H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1977, 45, 326; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Lightner, D. A. in "Analytical Applications of Circular Dichroism", Purdie, N.; Brittain, H. G. Eds., Elsevier, Amsterdam 1994, p. 131; "Circular Dichroism, Principles and Applications", Nakanishi, K.; Berova, N.; Woody, R. W.; Eds., VCH Publishers, New York, 1994.
15. 5. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S., Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C. H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1977, 45, 326; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Lightner, D. A. in "Analytical Applications of Circular Dichroism", Purdie, N.; Brittain, H. G. Eds., Elsevier, Amsterdam 1994, p. 131; "Circular Dichroism, Principles and Applications", Nakanishi, K.; Berova, N.; Woody, R. W.; Eds., VCH Publishers, New York, 1994.
16. 5. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S., Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C. H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1977, 45, 326; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Lightner, D. A. in "Analytical Applications of Circular Dichroism", Purdie, N.; Brittain, H. G. Eds., Elsevier, Amsterdam 1994, p. 131; "Circular Dichroism, Principles and Applications", Nakanishi, K.; Berova, N.; Woody, R. W.; Eds., VCH Publishers, New York, 1994.
17. 5. Burgstahler, A. W.; Barkhurst, R. C. J. Am. Chem. Soc. 1970, 92, 7601; Burgstahler, A. W.; Weigel, L. O.; Gawronski, J. K. Ibid. 1976, 98, 3015; Burgstahler, A. W.; Boger, D. L.; Naik, N. C. Tetrahedron 1976, 32, 309; Gawronski, J.; Gawronska, K. J. Chem. Soc., Chem. Commun. 1980, 346; Rosenfield, J. S., Charney, E. J. Am. Chem. Soc. 1977, 99, 3209; Charney, E.; Lee, C. H.; Rosenfield, J. S. Ibid. 1979, 101, 6802; Rauk, A.; Peoples, H. A. J. Comput. Chem. 1980, 1, 240; Bouman, T. D.; Hansen, A. E. Chem. Phys. Lett. 1977, 45, 326; see also: Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3695; 1971, 27, 4787; Hudec, J.; Kirk, D. N. Ibid. 1976, 32, 2475; Lightner, D. A. in "Analytical Applications of Circular Dichroism", Purdie, N.; Brittain, H. G. Eds., Elsevier, Amsterdam 1994, p. 131; "Circular Dichroism, Principles and Applications", Nakanishi, K.; Berova, N.; Woody, R. W.; Eds., VCH Publishers, New York, 1994.
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