A triple cascade sequence as a strategy for the construction of the erythrinane skeleton

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 1144-1155

  Padwa, Albert ^a   Hennig, Rudiger ^a   Oliver Kappe, C ^a   Reger, Thomas S ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ERYSOTRAMIDINE; ERYTHRINA ALKALOID; INDOLOISOQUINOLINE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; HYDROLYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0032549048     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9716183     Document Type: Article

References (116)

1. Boekelheide, V. Alkaloids 1960, 7, 201. Hill, R. K. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, p 483. Dyke, S. F.; Quessy, S. N. In The Alkaloids; Rodrigo, R. G. A., Ed.; Academic Press: New York, 1981; Vol. 18, p 1. Jackson, A. H. In The Chemistry and Biology of Isoquinoline Alkaloids; Phillipson, J. D., Roberts, M. F., Zenk, M. H., Eds.; Springer: Berlin, 1985; p 62.
2. Boekelheide, V. Alkaloids 1960, 7, 201. Hill, R. K. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, p 483. Dyke, S. F.; Quessy, S. N. In The Alkaloids; Rodrigo, R. G. A., Ed.; Academic Press: New York, 1981; Vol. 18, p 1. Jackson, A. H. In The Chemistry and Biology of Isoquinoline Alkaloids; Phillipson, J. D., Roberts, M. F., Zenk, M. H., Eds.; Springer: Berlin, 1985; p 62.
3. Boekelheide, V. Alkaloids 1960, 7, 201. Hill, R. K. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, p 483. Dyke, S. F.; Quessy, S. N. In The Alkaloids; Rodrigo, R. G. A., Ed.; Academic Press: New York, 1981; Vol. 18, p 1. Jackson, A. H. In The Chemistry and Biology of Isoquinoline Alkaloids; Phillipson, J. D., Roberts, M. F., Zenk, M. H., Eds.; Springer: Berlin, 1985; p 62.
4. Boekelheide, V. Alkaloids 1960, 7, 201. Hill, R. K. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, p 483. Dyke, S. F.; Quessy, S. N. In The Alkaloids; Rodrigo, R. G. A., Ed.; Academic Press: New York, 1981; Vol. 18, p 1. Jackson, A. H. In The Chemistry and Biology of Isoquinoline Alkaloids; Phillipson, J. D., Roberts, M. F., Zenk, M. H., Eds.; Springer: Berlin, 1985; p 62.
5. Chawla, A. S.; Jackson, A. H. Nat. Prod. Rep. 1984, 371. Ibid. 1986, 355. Ibid. 1989, 55. Ibid. 1990, 565. Bentley, K. W. Nat. Prod. Rep. 1991, 339. Ibid. 1992, 365. Ibid. 1993, 449. Ibid. 1994, 555. Ibid. 1995, 419.
6. Chawla, A. S.; Jackson, A. H. Nat. Prod. Rep. 1984, 371. Ibid. 1986, 355. Ibid. 1989, 55. Ibid. 1990, 565. Bentley, K. W. Nat. Prod. Rep. 1991, 339. Ibid. 1992, 365. Ibid. 1993, 449. Ibid. 1994, 555. Ibid. 1995, 419.
7. Chawla, A. S.; Jackson, A. H. Nat. Prod. Rep. 1984, 371. Ibid. 1986, 355. Ibid. 1989, 55. Ibid. 1990, 565. Bentley, K. W. Nat. Prod. Rep. 1991, 339. Ibid. 1992, 365. Ibid. 1993, 449. Ibid. 1994, 555. Ibid. 1995, 419.
8. Chawla, A. S.; Jackson, A. H. Nat. Prod. Rep. 1984, 371. Ibid. 1986, 355. Ibid. 1989, 55. Ibid. 1990, 565. Bentley, K. W. Nat. Prod. Rep. 1991, 339. Ibid. 1992, 365. Ibid. 1993, 449. Ibid. 1994, 555. Ibid. 1995, 419.
9. Chawla, A. S.; Jackson, A. H. Nat. Prod. Rep. 1984, 371. Ibid. 1986, 355. Ibid. 1989, 55. Ibid. 1990, 565. Bentley, K. W. Nat. Prod. Rep. 1991, 339. Ibid. 1992, 365. Ibid. 1993, 449. Ibid. 1994, 555. Ibid. 1995, 419.
10. Chawla, A. S.; Jackson, A. H. Nat. Prod. Rep. 1984, 371. Ibid. 1986, 355. Ibid. 1989, 55. Ibid. 1990, 565. Bentley, K. W. Nat. Prod. Rep. 1991, 339. Ibid. 1992, 365. Ibid. 1993, 449. Ibid. 1994, 555. Ibid. 1995, 419.
11. Chawla, A. S.; Jackson, A. H. Nat. Prod. Rep. 1984, 371. Ibid. 1986, 355. Ibid. 1989, 55. Ibid. 1990, 565. Bentley, K. W. Nat. Prod. Rep. 1991, 339. Ibid. 1992, 365. Ibid. 1993, 449. Ibid. 1994, 555. Ibid. 1995, 419.
12. Chawla, A. S.; Jackson, A. H. Nat. Prod. Rep. 1984, 371. Ibid. 1986, 355. Ibid. 1989, 55. Ibid. 1990, 565. Bentley, K. W. Nat. Prod. Rep. 1991, 339. Ibid. 1992, 365. Ibid. 1993, 449. Ibid. 1994, 555. Ibid. 1995, 419.
13. Chawla, A. S.; Jackson, A. H. Nat. Prod. Rep. 1984, 371. Ibid. 1986, 355. Ibid. 1989, 55. Ibid. 1990, 565. Bentley, K. W. Nat. Prod. Rep. 1991, 339. Ibid. 1992, 365. Ibid. 1993, 449. Ibid. 1994, 555. Ibid. 1995, 419.
14. Deulofeu, V.; In Curare and Curarelike Agents; Bovct, D., Bovet-Nitti, F., Marini-Bettolo, G. B., Eds; Elsevier: Amsterdam, 1959; p 163. Williams, M.; Robinson, J. L. J. Neurosci. 1984, 4, 2906. Decker, M. W.; Anderson, D. J.; Brioni, J. D.; Donnelly-Roberts, D. L.; Kang, C. H.; O'Neill, A. B.; Piattoni-Kaplan, M.; Swanson, S.; Sullivan, J. P. Eur. J. Pharmacol. 1995, 280, 79.
15. Deulofeu, V.; In Curare and Curarelike Agents; Bovct, D., Bovet-Nitti, F., Marini-Bettolo, G. B., Eds; Elsevier: Amsterdam, 1959; p 163. Williams, M.; Robinson, J. L. J. Neurosci. 1984, 4, 2906. Decker, M. W.; Anderson, D. J.; Brioni, J. D.; Donnelly-Roberts, D. L.; Kang, C. H.; O'Neill, A. B.; Piattoni-Kaplan, M.; Swanson, S.; Sullivan, J. P. Eur. J. Pharmacol. 1995, 280, 79.
16. Deulofeu, V.; In Curare and Curarelike Agents; Bovct, D., Bovet-Nitti, F., Marini-Bettolo, G. B., Eds; Elsevier: Amsterdam, 1959; p 163. Williams, M.; Robinson, J. L. J. Neurosci. 1984, 4, 2906. Decker, M. W.; Anderson, D. J.; Brioni, J. D.; Donnelly-Roberts, D. L.; Kang, C. H.; O'Neill, A. B.; Piattoni-Kaplan, M.; Swanson, S.; Sullivan, J. P. Eur. J. Pharmacol. 1995, 280, 79.
17. Mondon, A. Chem. Ber. 1959, 92, 1461. Ibid. 1959, 92, 1472. Mondon, A.; Hansen, K. F. Tetrahedron Lett. 1960, 5. Mondon, A.; Nestler, H. J. Angew. Chem., Int. Ed. Engl. 1964, 3, 588. Sano, T.; Toda, J.; Kashiwaba, N.; Oshima, T.; Tsuda, Y. Chem. Pharm. Bull. 1987, 35, 479. Sano, T. J. Org. Chem. 1985, 50, 5667. Ahmad-Schofiel, R.; Mariano, P. S. J. Org. Chem. 1987, 52, 1478. Ishibashi, H.; Sato, T.; Takahashi, M.; Hayashi, M.; Ikeda, M. Heterocycles 1988, 27, 2787.
18. Mondon, A. Chem. Ber. 1959, 92, 1461. Ibid. 1959, 92, 1472. Mondon, A.; Hansen, K. F. Tetrahedron Lett. 1960, 5. Mondon, A.; Nestler, H. J. Angew. Chem., Int. Ed. Engl. 1964, 3, 588. Sano, T.; Toda, J.; Kashiwaba, N.; Oshima, T.; Tsuda, Y. Chem. Pharm. Bull. 1987, 35, 479. Sano, T. J. Org. Chem. 1985, 50, 5667. Ahmad-Schofiel, R.; Mariano, P. S. J. Org. Chem. 1987, 52, 1478. Ishibashi, H.; Sato, T.; Takahashi, M.; Hayashi, M.; Ikeda, M. Heterocycles 1988, 27, 2787.
19. Mondon, A. Chem. Ber. 1959, 92, 1461. Ibid. 1959, 92, 1472. Mondon, A.; Hansen, K. F. Tetrahedron Lett. 1960, 5. Mondon, A.; Nestler, H. J. Angew. Chem., Int. Ed. Engl. 1964, 3, 588. Sano, T.; Toda, J.; Kashiwaba, N.; Oshima, T.; Tsuda, Y. Chem. Pharm. Bull. 1987, 35, 479. Sano, T. J. Org. Chem. 1985, 50, 5667. Ahmad-Schofiel, R.; Mariano, P. S. J. Org. Chem. 1987, 52, 1478. Ishibashi, H.; Sato, T.; Takahashi, M.; Hayashi, M.; Ikeda, M. Heterocycles 1988, 27, 2787.
20. Mondon, A. Chem. Ber. 1959, 92, 1461. Ibid. 1959, 92, 1472. Mondon, A.; Hansen, K. F. Tetrahedron Lett. 1960, 5. Mondon, A.; Nestler, H. J. Angew. Chem., Int. Ed. Engl. 1964, 3, 588. Sano, T.; Toda, J.; Kashiwaba, N.; Oshima, T.; Tsuda, Y. Chem. Pharm. Bull. 1987, 35, 479. Sano, T. J. Org. Chem. 1985, 50, 5667. Ahmad-Schofiel, R.; Mariano, P. S. J. Org. Chem. 1987, 52, 1478. Ishibashi, H.; Sato, T.; Takahashi, M.; Hayashi, M.; Ikeda, M. Heterocycles 1988, 27, 2787.
21. Mondon, A. Chem. Ber. 1959, 92, 1461. Ibid. 1959, 92, 1472. Mondon, A.; Hansen, K. F. Tetrahedron Lett. 1960, 5. Mondon, A.; Nestler, H. J. Angew. Chem., Int. Ed. Engl. 1964, 3, 588. Sano, T.; Toda, J.; Kashiwaba, N.; Oshima, T.; Tsuda, Y. Chem. Pharm. Bull. 1987, 35, 479. Sano, T. J. Org. Chem. 1985, 50, 5667. Ahmad-Schofiel, R.; Mariano, P. S. J. Org. Chem. 1987, 52, 1478. Ishibashi, H.; Sato, T.; Takahashi, M.; Hayashi, M.; Ikeda, M. Heterocycles 1988, 27, 2787.
22. Mondon, A. Chem. Ber. 1959, 92, 1461. Ibid. 1959, 92, 1472. Mondon, A.; Hansen, K. F. Tetrahedron Lett. 1960, 5. Mondon, A.; Nestler, H. J. Angew. Chem., Int. Ed. Engl. 1964, 3, 588. Sano, T.; Toda, J.; Kashiwaba, N.; Oshima, T.; Tsuda, Y. Chem. Pharm. Bull. 1987, 35, 479. Sano, T. J. Org. Chem. 1985, 50, 5667. Ahmad-Schofiel, R.; Mariano, P. S. J. Org. Chem. 1987, 52, 1478. Ishibashi, H.; Sato, T.; Takahashi, M.; Hayashi, M.; Ikeda, M. Heterocycles 1988, 27, 2787.
23. Mondon, A. Chem. Ber. 1959, 92, 1461. Ibid. 1959, 92, 1472. Mondon, A.; Hansen, K. F. Tetrahedron Lett. 1960, 5. Mondon, A.; Nestler, H. J. Angew. Chem., Int. Ed. Engl. 1964, 3, 588. Sano, T.; Toda, J.; Kashiwaba, N.; Oshima, T.; Tsuda, Y. Chem. Pharm. Bull. 1987, 35, 479. Sano, T. J. Org. Chem. 1985, 50, 5667. Ahmad-Schofiel, R.; Mariano, P. S. J. Org. Chem. 1987, 52, 1478. Ishibashi, H.; Sato, T.; Takahashi, M.; Hayashi, M.; Ikeda, M. Heterocycles 1988, 27, 2787.
24. Mondon, A. Chem. Ber. 1959, 92, 1461. Ibid. 1959, 92, 1472. Mondon, A.; Hansen, K. F. Tetrahedron Lett. 1960, 5. Mondon, A.; Nestler, H. J. Angew. Chem., Int. Ed. Engl. 1964, 3, 588. Sano, T.; Toda, J.; Kashiwaba, N.; Oshima, T.; Tsuda, Y. Chem. Pharm. Bull. 1987, 35, 479. Sano, T. J. Org. Chem. 1985, 50, 5667. Ahmad-Schofiel, R.; Mariano, P. S. J. Org. Chem. 1987, 52, 1478. Ishibashi, H.; Sato, T.; Takahashi, M.; Hayashi, M.; Ikeda, M. Heterocycles 1988, 27, 2787.
25. Belleau, B. Can. J. Chem. 1957, 35, 651. Prelog, V.; Langemann, A,; Rodig, O.; Ternmah, M. Helv. Chim. Acta 1959, 42, 1301. Sugasawa, S.; Yoshikawa, H. Chem. Pharm. Bull. 1960, 8, 290. Müller, M.; Grossnickle, T. T.; Boekelheide, V. J. Am. Chem. Soc. 1959, 81, 3959.
26. Belleau, B. Can. J. Chem. 1957, 35, 651. Prelog, V.; Langemann, A,; Rodig, O.; Ternmah, M. Helv. Chim. Acta 1959, 42, 1301. Sugasawa, S.; Yoshikawa, H. Chem. Pharm. Bull. 1960, 8, 290. Müller, M.; Grossnickle, T. T.; Boekelheide, V. J. Am. Chem. Soc. 1959, 81, 3959.
27. Belleau, B. Can. J. Chem. 1957, 35, 651. Prelog, V.; Langemann, A,; Rodig, O.; Ternmah, M. Helv. Chim. Acta 1959, 42, 1301. Sugasawa, S.; Yoshikawa, H. Chem. Pharm. Bull. 1960, 8, 290. Müller, M.; Grossnickle, T. T.; Boekelheide, V. J. Am. Chem. Soc. 1959, 81, 3959.
28. Belleau, B. Can. J. Chem. 1957, 35, 651. Prelog, V.; Langemann, A,; Rodig, O.; Ternmah, M. Helv. Chim. Acta 1959, 42, 1301. Sugasawa, S.; Yoshikawa, H. Chem. Pharm. Bull. 1960, 8, 290. Müller, M.; Grossnickle, T. T.; Boekelheide, V. J. Am. Chem. Soc. 1959, 81, 3959.
29. Tsuda, Y.; Sano, T. In Studies in Natural Products Chemistry, Rahman, A. U., Ed.; Elsevier: Amsterdam, 1989; Vol. 3, Part B, p 455.
30. Ho, T. L. Tandem Organic Reactions; Wiley: New York, 1992. Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131. Waldmann, H. In Domino Reaction in Organic Synthesis Highlights; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 193-202. Wender, P. A., Ed. Frontiers in Organic Synthesis, Chem. Rev. 1996, 96, 1-600.
31. Ho, T. L. Tandem Organic Reactions; Wiley: New York, 1992. Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131. Waldmann, H. In Domino Reaction in Organic Synthesis Highlights; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 193-202. Wender, P. A., Ed. Frontiers in Organic Synthesis, Chem. Rev. 1996, 96, 1-600.
32. Ho, T. L. Tandem Organic Reactions; Wiley: New York, 1992. Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131. Waldmann, H. In Domino Reaction in Organic Synthesis Highlights; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 193-202. Wender, P. A., Ed. Frontiers in Organic Synthesis, Chem. Rev. 1996, 96, 1-600.
33. Ho, T. L. Tandem Organic Reactions; Wiley: New York, 1992. Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131. Waldmann, H. In Domino Reaction in Organic Synthesis Highlights; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 193-202. Wender, P. A., Ed. Frontiers in Organic Synthesis, Chem. Rev. 1996, 96, 1-600.
34. For a recent classification of cascade/domino reactions, see: Tietze, L. F. Chem. Rev. (Washington, D.C.) 1996, 96, 115.
35. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. Oppolzer, W. Synthesis 1978, 793. Brieger, G.; Bennet, J. N. Chem. Rev. (Washington, D.C.) 1980, 80, 63. Ciganek, E. Org. React. 1984, 32,1. Fallis, A. G, Can. J. Chem. 1984, 62, 183. Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Taber, D. F. Intramolecular Diels-Alder and Alder-Ene Reactions; Springer: Berlin, 1984.
36. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. Oppolzer, W. Synthesis 1978, 793. Brieger, G.; Bennet, J. N. Chem. Rev. (Washington, D.C.) 1980, 80, 63. Ciganek, E. Org. React. 1984, 32,1. Fallis, A. G, Can. J. Chem. 1984, 62, 183. Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Taber, D. F. Intramolecular Diels-Alder and Alder-Ene Reactions; Springer: Berlin, 1984.
37. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. Oppolzer, W. Synthesis 1978, 793. Brieger, G.; Bennet, J. N. Chem. Rev. (Washington, D.C.) 1980, 80, 63. Ciganek, E. Org. React. 1984, 32,1. Fallis, A. G, Can. J. Chem. 1984, 62, 183. Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Taber, D. F. Intramolecular Diels-Alder and Alder-Ene Reactions; Springer: Berlin, 1984.
38. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. Oppolzer, W. Synthesis 1978, 793. Brieger, G.; Bennet, J. N. Chem. Rev. (Washington, D.C.) 1980, 80, 63. Ciganek, E. Org. React. 1984, 32,1. Fallis, A. G, Can. J. Chem. 1984, 62, 183. Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Taber, D. F. Intramolecular Diels-Alder and Alder-Ene Reactions; Springer: Berlin, 1984.
39. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. Oppolzer, W. Synthesis 1978, 793. Brieger, G.; Bennet, J. N. Chem. Rev. (Washington, D.C.) 1980, 80, 63. Ciganek, E. Org. React. 1984, 32,1. Fallis, A. G, Can. J. Chem. 1984, 62, 183. Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Taber, D. F. Intramolecular Diels-Alder and Alder-Ene Reactions; Springer: Berlin, 1984.
40. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. Oppolzer, W. Synthesis 1978, 793. Brieger, G.; Bennet, J. N. Chem. Rev. (Washington, D.C.) 1980, 80, 63. Ciganek, E. Org. React. 1984, 32,1. Fallis, A. G, Can. J. Chem. 1984, 62, 183. Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Taber, D. F. Intramolecular Diels-Alder and Alder-Ene Reactions; Springer: Berlin, 1984.
41. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. Oppolzer, W. Synthesis 1978, 793. Brieger, G.; Bennet, J. N. Chem. Rev. (Washington, D.C.) 1980, 80, 63. Ciganek, E. Org. React. 1984, 32,1. Fallis, A. G, Can. J. Chem. 1984, 62, 183. Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Taber, D. F. Intramolecular Diels-Alder and Alder-Ene Reactions; Springer: Berlin, 1984.
42. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. Oppolzer, W. Synthesis 1978, 793. Brieger, G.; Bennet, J. N. Chem. Rev. (Washington, D.C.) 1980, 80, 63. Ciganek, E. Org. React. 1984, 32,1. Fallis, A. G, Can. J. Chem. 1984, 62, 183. Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. Craig, D. Chem. Soc. Rev. 1987, 16, 187. Taber, D. F. Intramolecular Diels-Alder and Alder-Ene Reactions; Springer: Berlin, 1984.
43. Roush, W. R.; In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, p 91.
44. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 1047-1082. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 32, p 271. Hart, D. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed; Wiley: New York, 1988; Vol. 6, p 227.
45. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 1047-1082. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 32, p 271. Hart, D. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed; Wiley: New York, 1988; Vol. 6, p 227.
46. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 1047-1082. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 32, p 271. Hart, D. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed; Wiley: New York, 1988; Vol. 6, p 227.
47. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 1047-1082. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 32, p 271. Hart, D. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed; Wiley: New York, 1988; Vol. 6, p 227.
48. For a preliminary report, see: Padwa, A.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1996, 61, 4888. Reger, T.; Padwa, A. Abstracts of the 16th ISHC meeting, Bozeman, Mt., 1997.
49. For a preliminary report, see: Padwa, A.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1996, 61, 4888. Reger, T.; Padwa, A. Abstracts of the 16th ISHC meeting, Bozeman, Mt., 1997.
50. Gewald, K. Chem. Ber. 1966, 99, 1002. Boyd, G. V.; Heatherington, K. J. Chem. Soc., Perkin Trans. 1 1973, 2523. Nixon, W. J.; Garland, J. T.; DeWitt-Blanton, C. Synthesis 1980, 56. Aran, V. J.; Soto, J. L. Synthesis 1982, 513. Semmelhack, M. F.; Park, J. Organomet. 1986, 5, 2550. Chatani, N.; Hanafusa, T. J. Org. Chem. 1987, 52, 4408. Cutler, S. J.; El-Kabbani, F.; Keane, C.; Fisher-Shore, S. L.; DeWitt-Blanton, C. Heterocycles 1990, 31, 651.
51. Gewald, K. Chem. Ber. 1966, 99, 1002. Boyd, G. V.; Heatherington, K. J. Chem. Soc., Perkin Trans. 1 1973, 2523. Nixon, W. J.; Garland, J. T.; DeWitt-Blanton, C. Synthesis 1980, 56. Aran, V. J.; Soto, J. L. Synthesis 1982, 513. Semmelhack, M. F.; Park, J. Organomet. 1986, 5, 2550. Chatani, N.; Hanafusa, T. J. Org. Chem. 1987, 52, 4408. Cutler, S. J.; El-Kabbani, F.; Keane, C.; Fisher-Shore, S. L.; DeWitt-Blanton, C. Heterocycles 1990, 31, 651.
52. Gewald, K. Chem. Ber. 1966, 99, 1002. Boyd, G. V.; Heatherington, K. J. Chem. Soc., Perkin Trans. 1 1973, 2523. Nixon, W. J.; Garland, J. T.; DeWitt-Blanton, C. Synthesis 1980, 56. Aran, V. J.; Soto, J. L. Synthesis 1982, 513. Semmelhack, M. F.; Park, J. Organomet. 1986, 5, 2550. Chatani, N.; Hanafusa, T. J. Org. Chem. 1987, 52, 4408. Cutler, S. J.; El-Kabbani, F.; Keane, C.; Fisher-Shore, S. L.; DeWitt-Blanton, C. Heterocycles 1990, 31, 651.
53. Gewald, K. Chem. Ber. 1966, 99, 1002. Boyd, G. V.; Heatherington, K. J. Chem. Soc., Perkin Trans. 1 1973, 2523. Nixon, W. J.; Garland, J. T.; DeWitt-Blanton, C. Synthesis 1980, 56. Aran, V. J.; Soto, J. L. Synthesis 1982, 513. Semmelhack, M. F.; Park, J. Organomet. 1986, 5, 2550. Chatani, N.; Hanafusa, T. J. Org. Chem. 1987, 52, 4408. Cutler, S. J.; El-Kabbani, F.; Keane, C.; Fisher-Shore, S. L.; DeWitt-Blanton, C. Heterocycles 1990, 31, 651.
54. Gewald, K. Chem. Ber. 1966, 99, 1002. Boyd, G. V.; Heatherington, K. J. Chem. Soc., Perkin Trans. 1 1973, 2523. Nixon, W. J.; Garland, J. T.; DeWitt-Blanton, C. Synthesis 1980, 56. Aran, V. J.; Soto, J. L. Synthesis 1982, 513. Semmelhack, M. F.; Park, J. Organomet. 1986, 5, 2550. Chatani, N.; Hanafusa, T. J. Org. Chem. 1987, 52, 4408. Cutler, S. J.; El-Kabbani, F.; Keane, C.; Fisher-Shore, S. L.; DeWitt-Blanton, C. Heterocycles 1990, 31, 651.
55. Gewald, K. Chem. Ber. 1966, 99, 1002. Boyd, G. V.; Heatherington, K. J. Chem. Soc., Perkin Trans. 1 1973, 2523. Nixon, W. J.; Garland, J. T.; DeWitt-Blanton, C. Synthesis 1980, 56. Aran, V. J.; Soto, J. L. Synthesis 1982, 513. Semmelhack, M. F.; Park, J. Organomet. 1986, 5, 2550. Chatani, N.; Hanafusa, T. J. Org. Chem. 1987, 52, 4408. Cutler, S. J.; El-Kabbani, F.; Keane, C.; Fisher-Shore, S. L.; DeWitt-Blanton, C. Heterocycles 1990, 31, 651.
56. Gewald, K. Chem. Ber. 1966, 99, 1002. Boyd, G. V.; Heatherington, K. J. Chem. Soc., Perkin Trans. 1 1973, 2523. Nixon, W. J.; Garland, J. T.; DeWitt-Blanton, C. Synthesis 1980, 56. Aran, V. J.; Soto, J. L. Synthesis 1982, 513. Semmelhack, M. F.; Park, J. Organomet. 1986, 5, 2550. Chatani, N.; Hanafusa, T. J. Org. Chem. 1987, 52, 4408. Cutler, S. J.; El-Kabbani, F.; Keane, C.; Fisher-Shore, S. L.; DeWitt-Blanton, C. Heterocycles 1990, 31, 651.
57. Kappe, C. O.; Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 9285. Padwa, A.; Dimitroff, M.; Waterson, A. G.; Wu, T. J. Org. Chem. 1997, 62, 4088. Cochran, J. E.; Wu, T.; Padwa, A. Tetrahedron Lett. 1996, 37, 2903.
58. Kappe, C. O.; Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 9285. Padwa, A.; Dimitroff, M.; Waterson, A. G.; Wu, T. J. Org. Chem. 1997, 62, 4088. Cochran, J. E.; Wu, T.; Padwa, A. Tetrahedron Lett. 1996, 37, 2903.
59. Kappe, C. O.; Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 9285. Padwa, A.; Dimitroff, M.; Waterson, A. G.; Wu, T. J. Org. Chem. 1997, 62, 4088. Cochran, J. E.; Wu, T.; Padwa, A. Tetrahedron Lett. 1996, 37, 2903.
60. Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133. Schlessinger, R. H.; Wu, X. H.; Pettus, T. R. R. Synlett 1995, 536. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246. Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16.
61. Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133. Schlessinger, R. H.; Wu, X. H.; Pettus, T. R. R. Synlett 1995, 536. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246. Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16.
62. Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133. Schlessinger, R. H.; Wu, X. H.; Pettus, T. R. R. Synlett 1995, 536. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246. Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16.
63. Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133. Schlessinger, R. H.; Wu, X. H.; Pettus, T. R. R. Synlett 1995, 536. Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246. Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16.
64. Dunlop, A. P.; Peters, F. N.; In The Furans; Reinhold: New York, 1953; pp 170-192. Dean, F. M. Adv. Heterocycl. Chem. 1982, 37, 237. McClenaghan, L; Ramsden, C. A. J. Heterocycl. Chem. 1993, 30, 113.
65. Dunlop, A. P.; Peters, F. N.; In The Furans; Reinhold: New York, 1953; pp 170-192. Dean, F. M. Adv. Heterocycl. Chem. 1982, 37, 237. McClenaghan, L; Ramsden, C. A. J. Heterocycl. Chem. 1993, 30, 113.
66. Dunlop, A. P.; Peters, F. N.; In The Furans; Reinhold: New York, 1953; pp 170-192. Dean, F. M. Adv. Heterocycl. Chem. 1982, 37, 237. McClenaghan, L; Ramsden, C. A. J. Heterocycl. Chem. 1993, 30, 113.
67. Bite, P.; Ramonczai, J.; Vargha, L. J. Am. Chem. Soc. 1948, 70, 371. Edwards, W. R., Jr.; Singleton, H. M. J. Am. Chem. Soc. 1938, 60, 540. Marquis, R. Ann. Chim. Phys. 1905, 4, 196.
68. Bite, P.; Ramonczai, J.; Vargha, L. J. Am. Chem. Soc. 1948, 70, 371. Edwards, W. R., Jr.; Singleton, H. M. J. Am. Chem. Soc. 1938, 60, 540. Marquis, R. Ann. Chim. Phys. 1905, 4, 196.
69. Bite, P.; Ramonczai, J.; Vargha, L. J. Am. Chem. Soc. 1948, 70, 371. Edwards, W. R., Jr.; Singleton, H. M. J. Am. Chem. Soc. 1938, 60, 540. Marquis, R. Ann. Chim. Phys. 1905, 4, 196.
70. Freure, B. T.; Johnson, J. R. J. Am. Chem. Soc. 1931, 53, 3, 1142.
71. For a review of the Pummerer reaction and different triggering methods, see: DeLucchi, O.; Miotti, U.; Modena, G. Organic Reactions; Paquette, L. A., Ed.; John Wiley: 1991; Chapter 3, pp 157-184.
72. Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 3495.
73. For a review on isobenzofurans, see: Friedrichsen, W. Adv. Heterocycl. Chem. 1980, 26, 135. Rickborn, B. Advances in Theoretical Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1, p 1. Friedrichsen, W.; In Houben-Weyl, Methoden der Organischen Chemie; Kreher, R., Ed.; Thieme Verlag: Stuttgart, 1994; Vol. E6b, pp 163-216.
74. For a review on isobenzofurans, see: Friedrichsen, W. Adv. Heterocycl. Chem. 1980, 26, 135. Rickborn, B. Advances in Theoretical Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1, p 1. Friedrichsen, W.; In Houben-Weyl, Methoden der Organischen Chemie; Kreher, R., Ed.; Thieme Verlag: Stuttgart, 1994; Vol. E6b, pp 163-216.
75. For a review on isobenzofurans, see: Friedrichsen, W. Adv. Heterocycl. Chem. 1980, 26, 135. Rickborn, B. Advances in Theoretical Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1, p 1. Friedrichsen, W.; In Houben-Weyl, Methoden der Organischen Chemie; Kreher, R., Ed.; Thieme Verlag: Stuttgart, 1994; Vol. E6b, pp 163-216.
76. Cochran, J. E.; Padwa, A. J. Org. Chem. 1995, 60, 3938. Padwa, A.; Cochran, J. E.; Kappe, C. O. J. Org. Chem. 1996, 67, 3706.
77. Cochran, J. E.; Padwa, A. J. Org. Chem. 1995, 60, 3938. Padwa, A.; Cochran, J. E.; Kappe, C. O. J. Org. Chem. 1996, 67, 3706.
78. Padwa, A.; Kappe, C. O.; Cochran, J. E.; Snyder, J. P. J. Org. Chem. 1997, 62, 2786.
79. Watanabe, M.; Nakamori, S.; Hasegawa, H.; Shirai, K.; Kumamoto, T. Bull. Chem. Soc. Jpn. 1981, 54, 817.
80. Becke, A. D. J. Chem. Phys. 1993, 98, 5648. Stevens, P. J.; Devlin, F. F.; Chablowski, C. F.; Frisch, M. J. J. Chem. Phys. 1994, 99, 11623. Wiest, O.; Black, K. A.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10336.
81. Becke, A. D. J. Chem. Phys. 1993, 98, 5648. Stevens, P. J.; Devlin, F. F.; Chablowski, C. F.; Frisch, M. J. J. Chem. Phys. 1994, 99, 11623. Wiest, O.; Black, K. A.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10336.
82. Becke, A. D. J. Chem. Phys. 1993, 98, 5648. Stevens, P. J.; Devlin, F. F.; Chablowski, C. F.; Frisch, M. J. J. Chem. Phys. 1994, 99, 11623. Wiest, O.; Black, K. A.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10336.
83. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976.
84. Wilkens, H. J.; Traxler, F. Helv. Chim. Acta 1975, 58, 1512.
85. 26
86. Speckamp, W. N. Rec. Trav. Chim. Pays-Bas 1981, 700, 345. Maryanoff, B. E.; Rebarchak, M. C. Synthesis 1992, 1245.
87. Speckamp, W. N. Rec. Trav. Chim. Pays-Bas 1981, 700, 345. Maryanoff, B. E.; Rebarchak, M. C. Synthesis 1992, 1245.
88. For representative examples of .T-nucleophiles, see: Heaney, H.; Shuhaibar, K. F. Synlett 1995, 47. Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. Li, W. H.; Hanau, C. E.; Davignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. Logers, M.; Overman, L. E.; Welmalker, G. S. J. Am. Chem. Soc. 1995, 117, 9139. Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. Rigo, B.; Elghammarti, S.; Couturier, D. Tetrahedron Lett. 1996, 37, 485. Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054.
89. For representative examples of .T-nucleophiles, see: Heaney, H.; Shuhaibar, K. F. Synlett 1995, 47. Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. Li, W. H.; Hanau, C. E.; Davignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. Logers, M.; Overman, L. E.; Welmalker, G. S. J. Am. Chem. Soc. 1995, 117, 9139. Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. Rigo, B.; Elghammarti, S.; Couturier, D. Tetrahedron Lett. 1996, 37, 485. Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054.
90. For representative examples of .T-nucleophiles, see: Heaney, H.; Shuhaibar, K. F. Synlett 1995, 47. Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. Li, W. H.; Hanau, C. E.; Davignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. Logers, M.; Overman, L. E.; Welmalker, G. S. J. Am. Chem. Soc. 1995, 117, 9139. Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. Rigo, B.; Elghammarti, S.; Couturier, D. Tetrahedron Lett. 1996, 37, 485. Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054.
91. For representative examples of .T-nucleophiles, see: Heaney, H.; Shuhaibar, K. F. Synlett 1995, 47. Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. Li, W. H.; Hanau, C. E.; Davignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. Logers, M.; Overman, L. E.; Welmalker, G. S. J. Am. Chem. Soc. 1995, 117, 9139. Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. Rigo, B.; Elghammarti, S.; Couturier, D. Tetrahedron Lett. 1996, 37, 485. Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054.
92. For representative examples of .T-nucleophiles, see: Heaney, H.; Shuhaibar, K. F. Synlett 1995, 47. Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. Li, W. H.; Hanau, C. E.; Davignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. Logers, M.; Overman, L. E.; Welmalker, G. S. J. Am. Chem. Soc. 1995, 117, 9139. Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. Rigo, B.; Elghammarti, S.; Couturier, D. Tetrahedron Lett. 1996, 37, 485. Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054.
93. For representative examples of .T-nucleophiles, see: Heaney, H.; Shuhaibar, K. F. Synlett 1995, 47. Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. Li, W. H.; Hanau, C. E.; Davignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. Logers, M.; Overman, L. E.; Welmalker, G. S. J. Am. Chem. Soc. 1995, 117, 9139. Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. Rigo, B.; Elghammarti, S.; Couturier, D. Tetrahedron Lett. 1996, 37, 485. Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054.
94. For representative examples of .T-nucleophiles, see: Heaney, H.; Shuhaibar, K. F. Synlett 1995, 47. Lee, Y. S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149. Li, W. H.; Hanau, C. E.; Davignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155. Logers, M.; Overman, L. E.; Welmalker, G. S. J. Am. Chem. Soc. 1995, 117, 9139. Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107. Rigo, B.; Elghammarti, S.; Couturier, D. Tetrahedron Lett. 1996, 37, 485. Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996, 118, 1054.
95. Jones, G. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 2, p 438.
96. Gilchrist, T. L. Heterocyclic Chemistry; Pitman: London, 1981.
97. Kraus, G. A.; Raggon, J.; Thomas, P. J.; Bougie, D. Tetrahedron Lett. 1988, 29, 5605. Kraus, G. A.; Bougie, D.; Jacobsen, R. A.; Su, Y. J. Org. Chem. 1989, 54, 2425. Benson, S. C.; Li, J. H.; Snyder, J. K. J. Org. Chem. 1992, 57, 5285.
98. Kraus, G. A.; Raggon, J.; Thomas, P. J.; Bougie, D. Tetrahedron Lett. 1988, 29, 5605. Kraus, G. A.; Bougie, D.; Jacobsen, R. A.; Su, Y. J. Org. Chem. 1989, 54, 2425. Benson, S. C.; Li, J. H.; Snyder, J. K. J. Org. Chem. 1992, 57, 5285.
99. Kraus, G. A.; Raggon, J.; Thomas, P. J.; Bougie, D. Tetrahedron Lett. 1988, 29, 5605. Kraus, G. A.; Bougie, D.; Jacobsen, R. A.; Su, Y. J. Org. Chem. 1989, 54, 2425. Benson, S. C.; Li, J. H.; Snyder, J. K. J. Org. Chem. 1992, 57, 5285.
100. Corsico Coda, A.; Grünanger, P.; Vernesi, G. Tetrahedron Lett. 1966, 2911. Caramella, P.; Cellerino, G.; Corsico Coda, A.; Invernizzi, A. G.; Grünanger, P.; Houk, K. N.; Albini, F. M. J. Org. Chem. 1976, 41, 3349. Caramella, P. Tetrahedron Lett. 1968, 743. Caramella, P.; Cellerino, G.; Grünanger, P.; Albini, F. M.; Cellerino, M. R. Tetrahedron 1978, 34, 3545. Caramella, P.; Cellerino, G.; Houk, K. N.; Albini, F. M.; Santiago, C. J. Org. Chem. 1978, 43, 3006. Caramella, P.; Corsico Coda, A.; Corsaro, A.; Monte, D. D.; Albini, F. M. Tetrahedron 1982, 35, 173. Hassner, A.; Murthy, K. S. K.; Padwa, A.; Chiacchio, U.; Dean, D. C.; Schoffstall, A. M. J. Org. Chem. 1989, 54, 5277. Dehaen, W.; Hassner, A. J. Org. Chem. 1991, 56, 896. Yin, H.; Franck, R. W.; Chen, S. L.; Quigley, G. J.; Todaro, L. J. Org. Chem. 1992, 57, 644.
101. Corsico Coda, A.; Grünanger, P.; Vernesi, G. Tetrahedron Lett. 1966, 2911. Caramella, P.; Cellerino, G.; Corsico Coda, A.; Invernizzi, A. G.; Grünanger, P.; Houk, K. N.; Albini, F. M. J. Org. Chem. 1976, 41, 3349. Caramella, P. Tetrahedron Lett. 1968, 743. Caramella, P.; Cellerino, G.; Grünanger, P.; Albini, F. M.; Cellerino, M. R. Tetrahedron 1978, 34, 3545. Caramella, P.; Cellerino, G.; Houk, K. N.; Albini, F. M.; Santiago, C. J. Org. Chem. 1978, 43, 3006. Caramella, P.; Corsico Coda, A.; Corsaro, A.; Monte, D. D.; Albini, F. M. Tetrahedron 1982, 35, 173. Hassner, A.; Murthy, K. S. K.; Padwa, A.; Chiacchio, U.; Dean, D. C.; Schoffstall, A. M. J. Org. Chem. 1989, 54, 5277. Dehaen, W.; Hassner, A. J. Org. Chem. 1991, 56, 896. Yin, H.; Franck, R. W.; Chen, S. L.; Quigley, G. J.; Todaro, L. J. Org. Chem. 1992, 57, 644.
102. Corsico Coda, A.; Grünanger, P.; Vernesi, G. Tetrahedron Lett. 1966, 2911. Caramella, P.; Cellerino, G.; Corsico Coda, A.; Invernizzi, A. G.; Grünanger, P.; Houk, K. N.; Albini, F. M. J. Org. Chem. 1976, 41, 3349. Caramella, P. Tetrahedron Lett. 1968, 743. Caramella, P.; Cellerino, G.; Grünanger, P.; Albini, F. M.; Cellerino, M. R. Tetrahedron 1978, 34, 3545. Caramella, P.; Cellerino, G.; Houk, K. N.; Albini, F. M.; Santiago, C. J. Org. Chem. 1978, 43, 3006. Caramella, P.; Corsico Coda, A.; Corsaro, A.; Monte, D. D.; Albini, F. M. Tetrahedron 1982, 35, 173. Hassner, A.; Murthy, K. S. K.; Padwa, A.; Chiacchio, U.; Dean, D. C.; Schoffstall, A. M. J. Org. Chem. 1989, 54, 5277. Dehaen, W.; Hassner, A. J. Org. Chem. 1991, 56, 896. Yin, H.; Franck, R. W.; Chen, S. L.; Quigley, G. J.; Todaro, L. J. Org. Chem. 1992, 57, 644.
103. Corsico Coda, A.; Grünanger, P.; Vernesi, G. Tetrahedron Lett. 1966, 2911. Caramella, P.; Cellerino, G.; Corsico Coda, A.; Invernizzi, A. G.; Grünanger, P.; Houk, K. N.; Albini, F. M. J. Org. Chem. 1976, 41, 3349. Caramella, P. Tetrahedron Lett. 1968, 743. Caramella, P.; Cellerino, G.; Grünanger, P.; Albini, F. M.; Cellerino, M. R. Tetrahedron 1978, 34, 3545. Caramella, P.; Cellerino, G.; Houk, K. N.; Albini, F. M.; Santiago, C. J. Org. Chem. 1978, 43, 3006. Caramella, P.; Corsico Coda, A.; Corsaro, A.; Monte, D. D.; Albini, F. M. Tetrahedron 1982, 35, 173. Hassner, A.; Murthy, K. S. K.; Padwa, A.; Chiacchio, U.; Dean, D. C.; Schoffstall, A. M. J. Org. Chem. 1989, 54, 5277. Dehaen, W.; Hassner, A. J. Org. Chem. 1991, 56, 896. Yin, H.; Franck, R. W.; Chen, S. L.; Quigley, G. J.; Todaro, L. J. Org. Chem. 1992, 57, 644.
104. Corsico Coda, A.; Grünanger, P.; Vernesi, G. Tetrahedron Lett. 1966, 2911. Caramella, P.; Cellerino, G.; Corsico Coda, A.; Invernizzi, A. G.; Grünanger, P.; Houk, K. N.; Albini, F. M. J. Org. Chem. 1976, 41, 3349. Caramella, P. Tetrahedron Lett. 1968, 743. Caramella, P.; Cellerino, G.; Grünanger, P.; Albini, F. M.; Cellerino, M. R. Tetrahedron 1978, 34, 3545. Caramella, P.; Cellerino, G.; Houk, K. N.; Albini, F. M.; Santiago, C. J. Org. Chem. 1978, 43, 3006. Caramella, P.; Corsico Coda, A.; Corsaro, A.; Monte, D. D.; Albini, F. M. Tetrahedron 1982, 35, 173. Hassner, A.; Murthy, K. S. K.; Padwa, A.; Chiacchio, U.; Dean, D. C.; Schoffstall, A. M. J. Org. Chem. 1989, 54, 5277. Dehaen, W.; Hassner, A. J. Org. Chem. 1991, 56, 896. Yin, H.; Franck, R. W.; Chen, S. L.; Quigley, G. J.; Todaro, L. J. Org. Chem. 1992, 57, 644.
105. Corsico Coda, A.; Grünanger, P.; Vernesi, G. Tetrahedron Lett. 1966, 2911. Caramella, P.; Cellerino, G.; Corsico Coda, A.; Invernizzi, A. G.; Grünanger, P.; Houk, K. N.; Albini, F. M. J. Org. Chem. 1976, 41, 3349. Caramella, P. Tetrahedron Lett. 1968, 743. Caramella, P.; Cellerino, G.; Grünanger, P.; Albini, F. M.; Cellerino, M. R. Tetrahedron 1978, 34, 3545. Caramella, P.; Cellerino, G.; Houk, K. N.; Albini, F. M.; Santiago, C. J. Org. Chem. 1978, 43, 3006. Caramella, P.; Corsico Coda, A.; Corsaro, A.; Monte, D. D.; Albini, F. M. Tetrahedron 1982, 35, 173. Hassner, A.; Murthy, K. S. K.; Padwa, A.; Chiacchio, U.; Dean, D. C.; Schoffstall, A. M. J. Org. Chem. 1989, 54, 5277. Dehaen, W.; Hassner, A. J. Org. Chem. 1991, 56, 896. Yin, H.; Franck, R. W.; Chen, S. L.; Quigley, G. J.; Todaro, L. J. Org. Chem. 1992, 57, 644.
106. Corsico Coda, A.; Grünanger, P.; Vernesi, G. Tetrahedron Lett. 1966, 2911. Caramella, P.; Cellerino, G.; Corsico Coda, A.; Invernizzi, A. G.; Grünanger, P.; Houk, K. N.; Albini, F. M. J. Org. Chem. 1976, 41, 3349. Caramella, P. Tetrahedron Lett. 1968, 743. Caramella, P.; Cellerino, G.; Grünanger, P.; Albini, F. M.; Cellerino, M. R. Tetrahedron 1978, 34, 3545. Caramella, P.; Cellerino, G.; Houk, K. N.; Albini, F. M.; Santiago, C. J. Org. Chem. 1978, 43, 3006. Caramella, P.; Corsico Coda, A.; Corsaro, A.; Monte, D. D.; Albini, F. M. Tetrahedron 1982, 35, 173. Hassner, A.; Murthy, K. S. K.; Padwa, A.; Chiacchio, U.; Dean, D. C.; Schoffstall, A. M. J. Org. Chem. 1989, 54, 5277. Dehaen, W.; Hassner, A. J. Org. Chem. 1991, 56, 896. Yin, H.; Franck, R. W.; Chen, S. L.; Quigley, G. J.; Todaro, L. J. Org. Chem. 1992, 57, 644.
107. Corsico Coda, A.; Grünanger, P.; Vernesi, G. Tetrahedron Lett. 1966, 2911. Caramella, P.; Cellerino, G.; Corsico Coda, A.; Invernizzi, A. G.; Grünanger, P.; Houk, K. N.; Albini, F. M. J. Org. Chem. 1976, 41, 3349. Caramella, P. Tetrahedron Lett. 1968, 743. Caramella, P.; Cellerino, G.; Grünanger, P.; Albini, F. M.; Cellerino, M. R. Tetrahedron 1978, 34, 3545. Caramella, P.; Cellerino, G.; Houk, K. N.; Albini, F. M.; Santiago, C. J. Org. Chem. 1978, 43, 3006. Caramella, P.; Corsico Coda, A.; Corsaro, A.; Monte, D. D.; Albini, F. M. Tetrahedron 1982, 35, 173. Hassner, A.; Murthy, K. S. K.; Padwa, A.; Chiacchio, U.; Dean, D. C.; Schoffstall, A. M. J. Org. Chem. 1989, 54, 5277. Dehaen, W.; Hassner, A. J. Org. Chem. 1991, 56, 896. Yin, H.; Franck, R. W.; Chen, S. L.; Quigley, G. J.; Todaro, L. J. Org. Chem. 1992, 57, 644.
108. Corsico Coda, A.; Grünanger, P.; Vernesi, G. Tetrahedron Lett. 1966, 2911. Caramella, P.; Cellerino, G.; Corsico Coda, A.; Invernizzi, A. G.; Grünanger, P.; Houk, K. N.; Albini, F. M. J. Org. Chem. 1976, 41, 3349. Caramella, P. Tetrahedron Lett. 1968, 743. Caramella, P.; Cellerino, G.; Grünanger, P.; Albini, F. M.; Cellerino, M. R. Tetrahedron 1978, 34, 3545. Caramella, P.; Cellerino, G.; Houk, K. N.; Albini, F. M.; Santiago, C. J. Org. Chem. 1978, 43, 3006. Caramella, P.; Corsico Coda, A.; Corsaro, A.; Monte, D. D.; Albini, F. M. Tetrahedron 1982, 35, 173. Hassner, A.; Murthy, K. S. K.; Padwa, A.; Chiacchio, U.; Dean, D. C.; Schoffstall, A. M. J. Org. Chem. 1989, 54, 5277. Dehaen, W.; Hassner, A. J. Org. Chem. 1991, 56, 896. Yin, H.; Franck, R. W.; Chen, S. L.; Quigley, G. J.; Todaro, L. J. Org. Chem. 1992, 57, 644.
109. Jones, R. C. F.; Bates, A. D. Tetrahedron Lett. 1986, 27, 5285.
110. The authors have deposited coordinates for structure 38 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U. K.
111. McCague, R. Tetrahedron: Asymmetry 1990, 1, 97.
112. Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1984, 42, 4821.
113. Mukaiyama, T.; Kamio, K.; Kobayashi, S.; Takei, H. Bull Chem. Soc. Jpn. 1972, 45, 3723.
114. Tsuda, Y.; Hosoi, S.; Nakai, A.; Sakai, Y.; Abe, T.; Ishi, Y.; Kiuchi, F.; Sano, T. Chem. Pharm. Bull. 1991, 39, 1365.
115. Achiwa, K.; Chaloner, P. A.; Parker, D. J. Organomet. Chem. 1987, 218, 249.
116. Foote, C. S.; Kwon, B. M. J. Org. Chem. 1989, 54, 3878.