Synthesis of carbocycles via intramolecular conjugate additions: Another solution to the terpenoid side chain stereochemistry problem

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 465-472

  Guevel, Alyx Caroline ^a   Hart, David J ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANE DERIVATIVE; INDAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030047732     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951531m     Document Type: Article

References (58)

1. For one synthesis that addresses the side chain stereochemistry problem, see: Marino, J. P.; Abe, H. J. Am. Chem. Soc. 1981, 103, 2907.
2. For syntheses that address the side chain stereochemistry problem, see: Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735 and references cited therein.
3. For a synthesis that addresses the side chain stereochemistry problem, see: Guevel, A.-C.; Hart, D. J. Synlett 1994, 169; J. Org. Chem. 1996, 61, 473-479.
4. For a synthesis that addresses the side chain stereochemistry problem, see: Guevel, A.-C.; Hart, D. J. Synlett 1994, 169; J. Org. Chem. 1996, 61, 473-479.
5. For reviews, see: Piatak, D. M.; Wicha, J. Chem. Rev. 1978, 78, 199. Redpath, B. J.; Zeelen, F. J. Chem. Soc. Rev. 1983, 12, 75.
6. For reviews, see: Piatak, D. M.; Wicha, J. Chem. Rev. 1978, 78, 199. Redpath, B. J.; Zeelen, F. J. Chem. Soc. Rev. 1983, 12, 75.
7. For a categorization of more recent methods, see: Hart, D. J.; Krishnamurthy, R. Synlett 1991, 412. For some additional methods, see: Mandai, T.; Matsumoto, T.; Kawada. M. Tsuji, J. J. Org. Chem. 1992, 57, 6090. Kametani, T.; Katoh, T.; Tsubuki, M.; Honda, T. J. Am. Chem. Soc. 1986, 108, 7055. Evans, D. A.; Nelson, J. V. J. Am. Chem. Soc. 1980, 102, 774. Ficini, J.; D'Angelo, J.; Noire, J. J. Am. Chem. Soc. 1974, 96, 1213.
8. For a categorization of more recent methods, see: Hart, D. J.; Krishnamurthy, R. Synlett 1991, 412. For some additional methods, see: Mandai, T.; Matsumoto, T.; Kawada. M. Tsuji, J. J. Org. Chem. 1992, 57, 6090. Kametani, T.; Katoh, T.; Tsubuki, M.; Honda, T. J. Am. Chem. Soc. 1986, 108, 7055. Evans, D. A.; Nelson, J. V. J. Am. Chem. Soc. 1980, 102, 774. Ficini, J.; D'Angelo, J.; Noire, J. J. Am. Chem. Soc. 1974, 96, 1213.
9. For a categorization of more recent methods, see: Hart, D. J.; Krishnamurthy, R. Synlett 1991, 412. For some additional methods, see: Mandai, T.; Matsumoto, T.; Kawada. M. Tsuji, J. J. Org. Chem. 1992, 57, 6090. Kametani, T.; Katoh, T.; Tsubuki, M.; Honda, T. J. Am. Chem. Soc. 1986, 108, 7055. Evans, D. A.; Nelson, J. V. J. Am. Chem. Soc. 1980, 102, 774. Ficini, J.; D'Angelo, J.; Noire, J. J. Am. Chem. Soc. 1974, 96, 1213.
10. For a categorization of more recent methods, see: Hart, D. J.; Krishnamurthy, R. Synlett 1991, 412. For some additional methods, see: Mandai, T.; Matsumoto, T.; Kawada. M. Tsuji, J. J. Org. Chem. 1992, 57, 6090. Kametani, T.; Katoh, T.; Tsubuki, M.; Honda, T. J. Am. Chem. Soc. 1986, 108, 7055. Evans, D. A.; Nelson, J. V. J. Am. Chem. Soc. 1980, 102, 774. Ficini, J.; D'Angelo, J.; Noire, J. J. Am. Chem. Soc. 1974, 96, 1213.
11. For a categorization of more recent methods, see: Hart, D. J.; Krishnamurthy, R. Synlett 1991, 412. For some additional methods, see: Mandai, T.; Matsumoto, T.; Kawada. M. Tsuji, J. J. Org. Chem. 1992, 57, 6090. Kametani, T.; Katoh, T.; Tsubuki, M.; Honda, T. J. Am. Chem. Soc. 1986, 108, 7055. Evans, D. A.; Nelson, J. V. J. Am. Chem. Soc. 1980, 102, 774. Ficini, J.; D'Angelo, J.; Noire, J. J. Am. Chem. Soc. 1974, 96, 1213.
12. Chenera, B.; Chuang, C.-P.; Hart, D. J.; Lai, C.-S. J. Org. Chem. 1992, 57, 2018. This article also describes the preparation of aldehyde 12
13. Albaugh-Robertson, P.; Katzenellenbogen, J. A. J. Org. Chem. 1983, 48, 5288. For overviews of the Peterson olefination, see: Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M , Eds.; Pergamon Press: New York, 1991; Vol. 1, p 729. Chan, T.-H. Acc. Chem. Res. 1977, 10, 442.
14. Albaugh-Robertson, P.; Katzenellenbogen, J. A. J. Org. Chem. 1983, 48, 5288. For overviews of the Peterson olefination, see: Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M , Eds.; Pergamon Press: New York, 1991; Vol. 1, p 729. Chan, T.-H. Acc. Chem. Res. 1977, 10, 442.
15. Albaugh-Robertson, P.; Katzenellenbogen, J. A. J. Org. Chem. 1983, 48, 5288. For overviews of the Peterson olefination, see: Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M , Eds.; Pergamon Press: New York, 1991; Vol. 1, p 729. Chan, T.-H. Acc. Chem. Res. 1977, 10, 442.
16. House, H. O.; Jones, V. K.; Frank, G. A. J. Org. Chem. 1964, 29, 3327.
17. Henrick, C. A.; Willy, W. E.; Baum, J. W.; Baer, T. A ; Garcia, B. A.; Mastre, T. A.; Chang, S. M. J. Org. Chem. 1975, 40, 1. Schwarz, M.; Graminski, G. F.; Waters, R. M. J. Org. Chem. 1986, 51, 260. Annuziata, R.; Cinquini, M.; Cozzi, F.; Gennari, C.; Raimondi, L. J. Org. Chem 1987, 52, 4674.
18. Henrick, C. A.; Willy, W. E.; Baum, J. W.; Baer, T. A ; Garcia, B. A.; Mastre, T. A.; Chang, S. M. J. Org. Chem. 1975, 40, 1. Schwarz, M.; Graminski, G. F.; Waters, R. M. J. Org. Chem. 1986, 51, 260. Annuziata, R.; Cinquini, M.; Cozzi, F.; Gennari, C.; Raimondi, L. J. Org. Chem 1987, 52, 4674.
19. Henrick, C. A.; Willy, W. E.; Baum, J. W.; Baer, T. A ; Garcia, B. A.; Mastre, T. A.; Chang, S. M. J. Org. Chem. 1975, 40, 1. Schwarz, M.; Graminski, G. F.; Waters, R. M. J. Org. Chem. 1986, 51, 260. Annuziata, R.; Cinquini, M.; Cozzi, F.; Gennari, C.; Raimondi, L. J. Org. Chem 1987, 52, 4674.
20. Biernacki, W.; Gdula, A. Synthesis 1979, 37.
21. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
22. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
23. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
24. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
25. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
26. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
27. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
28. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
29. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
30. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
31. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
32. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
33. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
34. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
35. For pioneering studies related to the stereochemical course of Intramolecular conjugate additions, see: Stork, G.; Shiner, C. S.; Winkler, J. D. J Am. Chem. Soc 1982, 104, 310. For reviews of relevant conjugate additions, see: Hickmott, P. W. Tetrahedron 1982, 38, 1975. Hickmott, P. W.; Tetrahedron 1982, 38, 3363. Oare, D. A.; Heatheock, C. H. In Topics in Stereochemistry; Eliel. E. L., Wilen, S. H., Ed.; Wiley: New York, 1991; Vol. 26. Seebach, D.; Imwinkelried, R ; Weber, T. In Modern Synthetic Methods; Scheffold, R., Ed.: Springer-Verlag: Berlin, 1986; Vol. 4. Whitesell, J. K. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol. 6, p 703. For specific articles of interest, see: Massiot, G.: Mulamba, T. J. Chem. Soc., Chem. Commun. 1984, 715. Hirai, Y.; Hagiwara, A: Yamazaki, T. Heterocycles 1986, 24, 571. D'Angelo, J.; Desmaele, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459. Kozikowski, A. P.; Greco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873. Pandit, U. K.; Juisman, H. O. Tetrahedron Lett. 1967, 8, 3901. D'Angelo, J.; Gumgant, A.: Riche, C.; Chiaroni, A. Tetrahedron Lett 1988, 29, 2667. Guingant, A. Tetrahedron: Asymmetry 1991, 2, 415. Hori, K.; Kazuno, H.; Nomura, K.; Yoshii, E. Tetrahedron Lett. 1993, 34, 2183. Yoshii, E.; Hori, K ; Nomura, K.; Yamaguchi, Synlett 1995, 568.
36. We thank Dr. Judith C. Gallucci for performing X-ray crystallographic analyses of acids 20 and 36 at The Ohio State University Crystallography Facility.
37. 6 Thus, the observed epimerization is surely occurring at adjacent to the carbethoxy group.
38. Johnson, R. Chem. Rev. 1968, 68, 375. Huffman, R. W. Chem. Rev. 1989, 89, 1841.
39. Johnson, R. Chem. Rev. 1968, 68, 375. Huffman, R. W. Chem. Rev. 1989, 89, 1841.
40. Although the structures depicted in Scheme 5 are enolates, the same types of arguments could also be advanced for the corresponding enols.
41. Brattesam, D. N.; Heathcock, C. H. J. Org. Chem. 1975, 40, 2165.
42. Seebach, D.; Golinski, J. Helv. Chim. Acta 1981, 64, 1413. Blarer, S. J.; Schweizer, W. B.; Seebach, D. Helv. Chim. Acta 1982, 65, 1637.
43. Seebach, D.; Golinski, J. Helv. Chim. Acta 1981, 64, 1413. Blarer, S. J.; Schweizer, W. B.; Seebach, D. Helv. Chim. Acta 1982, 65, 1637.
44. Lanshury, P. T.; Haddon, V. R.; Stewart, R. C. J. Am. Chem. Soc. 1974, 96, 896. Hudlicky, T.; Govindan, S. V.; Frazier, J. O. J. Org. Chem. 1985, 50, 4166.
45. Lanshury, P. T.; Haddon, V. R.; Stewart, R. C. J. Am. Chem. Soc. 1974, 96, 896. Hudlicky, T.; Govindan, S. V.; Frazier, J. O. J. Org. Chem. 1985, 50, 4166.
46. Imamoto, T.; Kusumoto, T.; Tawarayama, T.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904.
47. Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682.
48. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015.
49. These conditions have been used to hydrolyze similar esters without epimerization at an adjacent stereogenic center. For example, see: Hart, D. J.; Huang, H.-C.; Krishnamurthy, R.; Schwartz, T. J. Am. Chem. Soc. 1989, 111, 7507.
50. For an approach to bicyclo[6.3.0]undecanes that affords transfused structures, see: Brooker-Milburn, K. I.; Thompson, D. F. Synlett 1993, 592. Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K Chem. Lett. 1993, 545.
51. For an approach to bicyclo[6.3.0]undecanes that affords transfused structures, see: Brooker-Milburn, K. I.; Thompson, D. F. Synlett 1993, 592. Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K Chem. Lett. 1993, 545.
52. Kauffman, G. B.; Pinnell, R. P. Inorg. Synth. 1960, 6, 3. Kauffman, G. B.; Teter, L. A. Inorg Synth. 1963, 7, 9. Linstrumelle, G.; Krieger, J. K.; Whitesides, G. M. Org. Synth. 1977, 55, 103.
53. Kauffman, G. B.; Pinnell, R. P. Inorg. Synth. 1960, 6, 3. Kauffman, G. B.; Teter, L. A. Inorg Synth. 1963, 7, 9. Linstrumelle, G.; Krieger, J. K.; Whitesides, G. M. Org. Synth. 1977, 55, 103.
54. Kauffman, G. B.; Pinnell, R. P. Inorg. Synth. 1960, 6, 3. Kauffman, G. B.; Teter, L. A. Inorg Synth. 1963, 7, 9. Linstrumelle, G.; Krieger, J. K.; Whitesides, G. M. Org. Synth. 1977, 55, 103.
55. Watson, S. C.; Eastham, J. F. J. Organomet. Chem. 1967, 9, 165.
56. Garbisch, E. W., Jr. J. Org. Chem. 1965, 30, 2109. Meier, H.; Antony-Mayer, C., Schulz-Popitz, C.; Zerban, G. Liebigs Ann. Chem. 1987, 1087. Mihelich, E. D.; Eickhoff, D. J. J. Org. Chem. 1983, 48, 4135.
57. Garbisch, E. W., Jr. J. Org. Chem. 1965, 30, 2109. Meier, H.; Antony-Mayer, C., Schulz-Popitz, C.; Zerban, G. Liebigs Ann. Chem. 1987, 1087. Mihelich, E. D.; Eickhoff, D. J. J. Org. Chem. 1983, 48, 4135.
58. Garbisch, E. W., Jr. J. Org. Chem. 1965, 30, 2109. Meier, H.; Antony-Mayer, C., Schulz-Popitz, C.; Zerban, G. Liebigs Ann. Chem. 1987, 1087. Mihelich, E. D.; Eickhoff, D. J. J. Org. Chem. 1983, 48, 4135.