Rearrangement Approaches to Cyclic Skeletons. XIII. Total Synthesis of Triquinane Sesquiterpenes, (±)-Modhephene, and (±)-Isocomene, on the Basis of Formal Substitution at Both Bridgeheads of a Bicyclo[2.2.2]oct-5-en-2-one

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 1, 1998, Pages 231-242

  Uyehara, Tadao ^a   Murayama, Tomohiro ^a   Sakai, Katsunori ^a   Onda, Kayoko ^a   Ueno, Masako ^b   Sato, Toshio ^b  

^a UTSUNOMIYA UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001357160     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.231     Document Type: Article

References (57)

1. Part XII of this series, see: T. Uyehara, T. Inayama, T. Kobari, Y. Kimura, and N. Yoneta, Bull. Chem. Soc. Jpn., 70, 1919 (1997).
2. Preliminary communication of a part of this work, see: T. Uyehara, T. Murayama, K. Sakai, M. Ueno, and T. Sato, Tetrahedron Lett., 37, 7295 (1996).
3. For reviews, see: a) K. N. Houk, Chem. Rev., 76, 1 (1976); b) K. Schaffner and M. Demuth, "Modern Synthetic Method," ed by R. Scheffold, Splinger-Verlag, Berlin (1986), Vol. 4, pp. 61-88 and pp. 89-124.
4. For reviews, see: a) K. N. Houk, Chem. Rev., 76, 1 (1976); b) K. Schaffner and M. Demuth, "Modern Synthetic Method," ed by R. Scheffold, Splinger-Verlag, Berlin (1986), Vol. 4, pp. 61-88 and pp. 89-124.
5. For recent reviews, see: a) L. A. Paquette, Synlett, 1990, 67; b) L. A. Paquette, Angew. Chem., Int. Ed. Engl., 29, 609 (1990); S. R. Wilson, Org. Reaction, 43, 93 (1993).
6. For recent reviews, see: a) L. A. Paquette, Synlett, 1990, 67; b) L. A. Paquette, Angew. Chem., Int. Ed. Engl., 29, 609 (1990); S. R. Wilson, Org. Reaction, 43, 93 (1993).
7. For recent reviews, see: a) L. A. Paquette, Synlett, 1990, 67; b) L. A. Paquette, Angew. Chem., Int. Ed. Engl., 29, 609 (1990); S. R. Wilson, Org. Reaction, 43, 93 (1993).
8. a) T. Uyehara, J. Yamada, K. Ogata, and T. Kato, Bull. Chem. Soc. Jpn., 58, 211 (1985);
9. b) T. Uyehara, J. Yamada, T. Kato, and F. Bohlmann, Bull. Chem. Soc. Jpn., 58, 861 (1985);
10. c) T. Uyehara, Y. Kabasawa, T. Furuta, and T. Kato, Bull. Chem. Soc. Jpn., 59, 539 (1986);
11. d) T. Uyehara, Y. Kabasawa, and T. Kato, Bull. Chem. Soc. Jpn., 59, 2521 (1986);
12. e) T. Uyehara, J. Yamada, T. Furuta, T. Kato, and Y. Yamamoto, Tetrahedron, 43, 5605 (1987);
13. f) T. Uyehara, T. Furuta, Y. Kabasawa, J. Yamada, T. Kato, and Y. Yamamoto, J. Org. Chem., 54, 3669 (1988).
14. For a review, see: S. Ranganathan, D. Ranganathan, and A. K. Mehrotra, Synthesis, 1977, 289.
15. T. Uyehara, K. Osanai, M. Sugimoto, I. Suzuki, and Y. Yamamoto, J. Am. Chem. Soc., 111, 7264 (1989).
16. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
17. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
18. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
19. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
20. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
21. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
22. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
23. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
24. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
25. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
26. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
27. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
28. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
29. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
30. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
31. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
32. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
33. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
34. Isolation: a) L. H. Zalkow, R. N. Harris, III, and D. Van Derueer, J. Chem. Soc., Chem. Commun., 1978, 420; b) F. Bohlmann, C. Zdero, R. Bohlmann, R. M. King, and H. Robinson, Phytochem., 19, 579 (1980); Syntheses: c) M. Karpf and A. S. Dreiding, Tetrahedron Lett., 21, 4569 (1980); d) A. B. Smith, III and P. J. Jerris, J. Am. Chem. Soc., 103, 194 (1981); e) H. Schostarez and L. A. Paquette, J. Am. Chem. Soc., 103, 722 (1981); Tetrahedron, 37, 4431 (1981); f) W. Oppolzer and F. Marazza, Helv. Chim. Acta, 64, 1575 (1981); W. Oppolzer and K. Bättig, Helv. Chim. Acta, 64, 2489 (1981); g) A. B. Smith and P. J. Jerris, J. Org. Chem., 47, 1845 (1982); h) P. A. Wender and G. B. Dreyer, J. Am. Chem. Soc., 104, 5805 (1982); i) J. Wrobel, K. Takahashi, U. Honkan, G. Lannoye, J. M. Cook, and S. H. Bertz, J. Org. Chem., 48, 139 (1983); j) Y. Tobe, S. Yamashita, T. Yamashita, M. Kakiuchi, and Y. Ohdaira, J. Chem. Soc., Chem. Commun., 1984, 1259; k) D. Wilkening, B. P. Mundy, Tetrahedron Lett., 25, 4619 (1984); l) B. P. Mundy, D. Wilkening, and K. B. Lipkowitz, J. Org. Chem., 50, 5727 (1985); m) G. Mehta and D. Subrahmanyam, J. Chem. Soc., Chem. Commun., 1985, 768; J. Chem. Soc., Perkin Trans. 1, 1991, 395; n) E. A. Mash, S. K. Math, and C. J. Flann, Tetrahedron Lett., 29, 2147 (1988); o) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron Lett., 29, 5525 (1988); p) S. C. Suri, Tetrahedron Lett., 34, 8321 (1993).
35. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
36. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
37. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
38. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
39. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
40. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
41. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
42. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
43. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
44. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
45. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
46. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
47. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
48. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
49. Isolatoion: a) L. H. Zalkow, R. N. Harris, III, D. Van Derveer, and J. A. Bertrand, J. Chem. Soc., Chem. Commun., 1979, 456; b) F. Bohlmann, N. Le Van, and J. Pickardt, Chem. Ber., 110, 3777 (1977); Syntheses: c) L. A. Paquette and Y. K. Han, J. Org. Chem., 44, 4014 (1979); J. Am. Chem. Soc., 103, 1835 (1981); d) W. Oppolzer, K. Battig, and T. Hudlicky, Helv. Chim. Acta, 62, 1493 (1979); Tetrahedron, 37, 4359 (1981); e) M. C. Pirrung, J. Am. Chem. Soc., 101, 7130 (1979); J. Am. Chem. Soc., 103, 82 (1981); f) W. G. Dauben and D. M. Walker, J. Org. Chem., 46, 1103 (1981); g) P. A. Wender and G. B. Dreyer, Tetrahadron, 37, 4445 (1981); h) E. Wenkert and T. S. Arrhenius, J. Am. Chem. Soc., 105, 2030 (1983); i) Y. Tobe, T. Yamashita, K. Kakiuchi, and Y. Odaira, J. Chem. Soc., Chem. Commun., 1985, 898; j) G. G. G. Von Manzardo, M. Karpf, and A. Dreiding, Helv. Chim. Acta, 69, 659 (1986); k) L. Fitjer, M. Majewski, and H. Monzo-Oltra, Tetrahedron, 32, 8835 (1995); l) P. Seiler, L. Issacs, and F. Diederich, Helv. Chim. Acta, 79, 1047 (1996).
50. T. Uyehara, T. Inayama, T. Furuta, T. Kato, Y. Yamamoto, M. Ueno, and T. Sato, Bull. Chem. Soc. Jpn., 69, 1727 (1996), and references cited therein.
51. Application to sesquiterpene syntheses, for example, see: K. E. Stevens and P. Yates, J. Chem. Soc., Chem. Commun., 1980, 990; M. Demuth, Chemia, 38, 257 (1984); M. Demuth and W. Hinsken, Angew. Chem., Int. Ed. Engl., 24, 973 (1985); M. Demuth, Helv. Chem. Acta, 71, 569 (1988); Refs. 7 and 8m.
52. Application to sesquiterpene syntheses, for example, see: K. E. Stevens and P. Yates, J. Chem. Soc., Chem. Commun., 1980, 990; M. Demuth, Chemia, 38, 257 (1984); M. Demuth and W. Hinsken, Angew. Chem., Int. Ed. Engl., 24, 973 (1985); M. Demuth, Helv. Chem. Acta, 71, 569 (1988); Refs. 7 and 8m.
53. Application to sesquiterpene syntheses, for example, see: K. E. Stevens and P. Yates, J. Chem. Soc., Chem. Commun., 1980, 990; M. Demuth, Chemia, 38, 257 (1984); M. Demuth and W. Hinsken, Angew. Chem., Int. Ed. Engl., 24, 973 (1985); M. Demuth, Helv. Chem. Acta, 71, 569 (1988); Refs. 7 and 8m.
54. Application to sesquiterpene syntheses, for example, see: K. E. Stevens and P. Yates, J. Chem. Soc., Chem. Commun., 1980, 990; M. Demuth, Chemia, 38, 257 (1984); M. Demuth and W. Hinsken, Angew. Chem., Int. Ed. Engl., 24, 973 (1985); M. Demuth, Helv. Chem. Acta, 71, 569 (1988); Refs. 7 and 8m.
55. J. Tsuji, I. Minami, I. Simizu, and H. Kataoka, Chem. Lett., 1984, 1133.
56. T. Uyehara, N. Takehara, M. Ueno, and T. Sato, Bull. Chem. Soc. Jpn., 68, 2687 (1995), and Ref. 7.
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