New asymmetric construction of the benzylic quaternary stereogenic centre: An enantiocontrolled access to (-)-α-cuparenone

Chemical Communications

Volumn , Issue 13, 1997, Pages 1167-1168

  Kosaka, Takamitsu ^a   Bando, Toshikazu ^a   Shishido, Kozo ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002369237     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a702667f     Document Type: Article

References (34)

1. K. Fuji, Chem. Rev., 1993, 93, 2037.
2. T. Takemoto, M. Sodeoka, H. Sasai and M. Shibasaki, J. Am. Chem. Soc., 1993, 115, 8477.
3. For recent representative chiral syntheses of (-)-α-cuparenone; (a) A. I. Meyers and B. A. Lefker, J. Org. Chem., 1986, 51, 1541; (b) M. M. Gharpure and A. S. Rao, Synth. Commun., 1989, 19, 1813; (c) H. Nemoto, H. Ishibashi, M. Nagamochi and K. Fukumoto, J. Org. Chem., 1992, 57, 1707; (d) J. L. Canet, A. Fadel and J. Salaün, J. Org. Chem., 1992, 57, 3463, and references are cited therein. For (+)-α-cuparenone, (e) T. Honda, N. Kimura and M. Tsubuki, Tetrahedron Asymmetry, 1993, 4, 21; (f) J. B. Schwarz and A. I. Meyers, J. Org. Chem., 1995, 60, 6511; (g) K. Maruoka, M. Oishi and H. Yamamoto, J. Am. Chem. Soc., 1996, 118, 2289.
4. For recent representative chiral syntheses of (-)-α-cuparenone; (a) A. I. Meyers and B. A. Lefker, J. Org. Chem., 1986, 51, 1541; (b) M. M. Gharpure and A. S. Rao, Synth. Commun., 1989, 19, 1813; (c) H. Nemoto, H. Ishibashi, M. Nagamochi and K. Fukumoto, J. Org. Chem., 1992, 57, 1707; (d) J. L. Canet, A. Fadel and J. Salaün, J. Org. Chem., 1992, 57, 3463, and references are cited therein. For (+)-α-cuparenone, (e) T. Honda, N. Kimura and M. Tsubuki, Tetrahedron Asymmetry, 1993, 4, 21; (f) J. B. Schwarz and A. I. Meyers, J. Org. Chem., 1995, 60, 6511; (g) K. Maruoka, M. Oishi and H. Yamamoto, J. Am. Chem. Soc., 1996, 118, 2289.
5. For recent representative chiral syntheses of (-)-α-cuparenone; (a) A. I. Meyers and B. A. Lefker, J. Org. Chem., 1986, 51, 1541; (b) M. M. Gharpure and A. S. Rao, Synth. Commun., 1989, 19, 1813; (c) H. Nemoto, H. Ishibashi, M. Nagamochi and K. Fukumoto, J. Org. Chem., 1992, 57, 1707; (d) J. L. Canet, A. Fadel and J. Salaün, J. Org. Chem., 1992, 57, 3463, and references are cited therein. For (+)-α-cuparenone, (e) T. Honda, N. Kimura and M. Tsubuki, Tetrahedron Asymmetry, 1993, 4, 21; (f) J. B. Schwarz and A. I. Meyers, J. Org. Chem., 1995, 60, 6511; (g) K. Maruoka, M. Oishi and H. Yamamoto, J. Am. Chem. Soc., 1996, 118, 2289.
6. For recent representative chiral syntheses of (-)-α-cuparenone; (a) A. I. Meyers and B. A. Lefker, J. Org. Chem., 1986, 51, 1541; (b) M. M. Gharpure and A. S. Rao, Synth. Commun., 1989, 19, 1813; (c) H. Nemoto, H. Ishibashi, M. Nagamochi and K. Fukumoto, J. Org. Chem., 1992, 57, 1707; (d) J. L. Canet, A. Fadel and J. Salaün, J. Org. Chem., 1992, 57, 3463, and references are cited therein. For (+)-α-cuparenone, (e) T. Honda, N. Kimura and M. Tsubuki, Tetrahedron Asymmetry, 1993, 4, 21; (f) J. B. Schwarz and A. I. Meyers, J. Org. Chem., 1995, 60, 6511; (g) K. Maruoka, M. Oishi and H. Yamamoto, J. Am. Chem. Soc., 1996, 118, 2289.
7. For recent representative chiral syntheses of (-)-α-cuparenone; (a) A. I. Meyers and B. A. Lefker, J. Org. Chem., 1986, 51, 1541; (b) M. M. Gharpure and A. S. Rao, Synth. Commun., 1989, 19, 1813; (c) H. Nemoto, H. Ishibashi, M. Nagamochi and K. Fukumoto, J. Org. Chem., 1992, 57, 1707; (d) J. L. Canet, A. Fadel and J. Salaün, J. Org. Chem., 1992, 57, 3463, and references are cited therein. For (+)-α-cuparenone, (e) T. Honda, N. Kimura and M. Tsubuki, Tetrahedron Asymmetry, 1993, 4, 21; (f) J. B. Schwarz and A. I. Meyers, J. Org. Chem., 1995, 60, 6511; (g) K. Maruoka, M. Oishi and H. Yamamoto, J. Am. Chem. Soc., 1996, 118, 2289.
8. For recent representative chiral syntheses of (-)-α-cuparenone; (a) A. I. Meyers and B. A. Lefker, J. Org. Chem., 1986, 51, 1541; (b) M. M. Gharpure and A. S. Rao, Synth. Commun., 1989, 19, 1813; (c) H. Nemoto, H. Ishibashi, M. Nagamochi and K. Fukumoto, J. Org. Chem., 1992, 57, 1707; (d) J. L. Canet, A. Fadel and J. Salaün, J. Org. Chem., 1992, 57, 3463, and references are cited therein. For (+)-α-cuparenone, (e) T. Honda, N. Kimura and M. Tsubuki, Tetrahedron Asymmetry, 1993, 4, 21; (f) J. B. Schwarz and A. I. Meyers, J. Org. Chem., 1995, 60, 6511; (g) K. Maruoka, M. Oishi and H. Yamamoto, J. Am. Chem. Soc., 1996, 118, 2289.
9. For recent representative chiral syntheses of (-)-α-cuparenone; (a) A. I. Meyers and B. A. Lefker, J. Org. Chem., 1986, 51, 1541; (b) M. M. Gharpure and A. S. Rao, Synth. Commun., 1989, 19, 1813; (c) H. Nemoto, H. Ishibashi, M. Nagamochi and K. Fukumoto, J. Org. Chem., 1992, 57, 1707; (d) J. L. Canet, A. Fadel and J. Salaün, J. Org. Chem., 1992, 57, 3463, and references are cited therein. For (+)-α-cuparenone, (e) T. Honda, N. Kimura and M. Tsubuki, Tetrahedron Asymmetry, 1993, 4, 21; (f) J. B. Schwarz and A. I. Meyers, J. Org. Chem., 1995, 60, 6511; (g) K. Maruoka, M. Oishi and H. Yamamoto, J. Am. Chem. Soc., 1996, 118, 2289.
10. For cyclopentene annulation via [1,5] C-H insertion of alkylidene carbene; (a) J. Wolinsky, G. W. Clark and P. C. Thorstenson, J. Org. Chem., 1976, 41, 745; (b) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251; (c) J. C. Gilbert, D. H. Giamalva and M. E. Baze, J. Org. Chem., 1985, 50, 2557; (d) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281; (e) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721; (g) M. Ochiai, K. Uemura and Y. Masaki, J. Am. Chem. Soc., 1993, 115, 2528; (h) S. Ohira, T. Moritani, T. Ida and M. Yamato, J. Chem. Soc., Chem. Commun., 1993, 1299; (i) R. R. Tykwinski, P. J. Stang and N. E. Persky, Tetrahedron Lett., 1994, 35, 23; (j) M. Kunishima, K. Hioki, S. Tani and A. Kato, Tetrahedron Lett., 1994, 35, 7253; (k) D. F. Taber and R. P. Meagley, Tetrahedron Lett., 1994, 35, 7909; (l) S. Kim and C. M. Cho, Tetrahedron Lett., 1994, 35, 8405; (m) D. F. Taber, A. Sahli, H. Yu and R. P. Meagley, J. Org. Chem., 1995, 60, 6571; (n) D. F. Taber, R. P. Meagley and D. J. Doren, J. Org. Chem., 1996, 61, 5723.
11. For cyclopentene annulation via [1,5] C-H insertion of alkylidene carbene; (a) J. Wolinsky, G. W. Clark and P. C. Thorstenson, J. Org. Chem., 1976, 41, 745; (b) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251; (c) J. C. Gilbert, D. H. Giamalva and M. E. Baze, J. Org. Chem., 1985, 50, 2557; (d) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281; (e) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721; (g) M. Ochiai, K. Uemura and Y. Masaki, J. Am. Chem. Soc., 1993, 115, 2528; (h) S. Ohira, T. Moritani, T. Ida and M. Yamato, J. Chem. Soc., Chem. Commun., 1993, 1299; (i) R. R. Tykwinski, P. J. Stang and N. E. Persky, Tetrahedron Lett., 1994, 35, 23; (j) M. Kunishima, K. Hioki, S. Tani and A. Kato, Tetrahedron Lett., 1994, 35, 7253; (k) D. F. Taber and R. P. Meagley, Tetrahedron Lett., 1994, 35, 7909; (l) S. Kim and C. M. Cho, Tetrahedron Lett., 1994, 35, 8405; (m) D. F. Taber, A. Sahli, H. Yu and R. P. Meagley, J. Org. Chem., 1995, 60, 6571; (n) D. F. Taber, R. P. Meagley and D. J. Doren, J. Org. Chem., 1996, 61, 5723.
12. For cyclopentene annulation via [1,5] C-H insertion of alkylidene carbene; (a) J. Wolinsky, G. W. Clark and P. C. Thorstenson, J. Org. Chem., 1976, 41, 745; (b) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251; (c) J. C. Gilbert, D. H. Giamalva and M. E. Baze, J. Org. Chem., 1985, 50, 2557; (d) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281; (e) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721; (g) M. Ochiai, K. Uemura and Y. Masaki, J. Am. Chem. Soc., 1993, 115, 2528; (h) S. Ohira, T. Moritani, T. Ida and M. Yamato, J. Chem. Soc., Chem. Commun., 1993, 1299; (i) R. R. Tykwinski, P. J. Stang and N. E. Persky, Tetrahedron Lett., 1994, 35, 23; (j) M. Kunishima, K. Hioki, S. Tani and A. Kato, Tetrahedron Lett., 1994, 35, 7253; (k) D. F. Taber and R. P. Meagley, Tetrahedron Lett., 1994, 35, 7909; (l) S. Kim and C. M. Cho, Tetrahedron Lett., 1994, 35, 8405; (m) D. F. Taber, A. Sahli, H. Yu and R. P. Meagley, J. Org. Chem., 1995, 60, 6571; (n) D. F. Taber, R. P. Meagley and D. J. Doren, J. Org. Chem., 1996, 61, 5723.
13. For cyclopentene annulation via [1,5] C-H insertion of alkylidene carbene; (a) J. Wolinsky, G. W. Clark and P. C. Thorstenson, J. Org. Chem., 1976, 41, 745; (b) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251; (c) J. C. Gilbert, D. H. Giamalva and M. E. Baze, J. Org. Chem., 1985, 50, 2557; (d) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281; (e) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721; (g) M. Ochiai, K. Uemura and Y. Masaki, J. Am. Chem. Soc., 1993, 115, 2528; (h) S. Ohira, T. Moritani, T. Ida and M. Yamato, J. Chem. Soc., Chem. Commun., 1993, 1299; (i) R. R. Tykwinski, P. J. Stang and N. E. Persky, Tetrahedron Lett., 1994, 35, 23; (j) M. Kunishima, K. Hioki, S. Tani and A. Kato, Tetrahedron Lett., 1994, 35, 7253; (k) D. F. Taber and R. P. Meagley, Tetrahedron Lett., 1994, 35, 7909; (l) S. Kim and C. M. Cho, Tetrahedron Lett., 1994, 35, 8405; (m) D. F. Taber, A. Sahli, H. Yu and R. P. Meagley, J. Org. Chem., 1995, 60, 6571; (n) D. F. Taber, R. P. Meagley and D. J. Doren, J. Org. Chem., 1996, 61, 5723.
14. For cyclopentene annulation via [1,5] C-H insertion of alkylidene carbene; (a) J. Wolinsky, G. W. Clark and P. C. Thorstenson, J. Org. Chem., 1976, 41, 745; (b) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251; (c) J. C. Gilbert, D. H. Giamalva and M. E. Baze, J. Org. Chem., 1985, 50, 2557; (d) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281; (e) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721; (g) M. Ochiai, K. Uemura and Y. Masaki, J. Am. Chem. Soc., 1993, 115, 2528; (h) S. Ohira, T. Moritani, T. Ida and M. Yamato, J. Chem. Soc., Chem. Commun., 1993, 1299; (i) R. R. Tykwinski, P. J. Stang and N. E. Persky, Tetrahedron Lett., 1994, 35, 23; (j) M. Kunishima, K. Hioki, S. Tani and A. Kato, Tetrahedron Lett., 1994, 35, 7253; (k) D. F. Taber and R. P. Meagley, Tetrahedron Lett., 1994, 35, 7909; (l) S. Kim and C. M. Cho, Tetrahedron Lett., 1994, 35, 8405; (m) D. F. Taber, A. Sahli, H. Yu and R. P. Meagley, J. Org. Chem., 1995, 60, 6571; (n) D. F. Taber, R. P. Meagley and D. J. Doren, J. Org. Chem., 1996, 61, 5723.
15. For cyclopentene annulation via [1,5] C-H insertion of alkylidene carbene; (a) J. Wolinsky, G. W. Clark and P. C. Thorstenson, J. Org. Chem., 1976, 41, 745; (b) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251; (c) J. C. Gilbert, D. H. Giamalva and M. E. Baze, J. Org. Chem., 1985, 50, 2557; (d) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281; (e) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721; (g) M. Ochiai, K. Uemura and Y. Masaki, J. Am. Chem. Soc., 1993, 115, 2528; (h) S. Ohira, T. Moritani, T. Ida and M. Yamato, J. Chem. Soc., Chem. Commun., 1993, 1299; (i) R. R. Tykwinski, P. J. Stang and N. E. Persky, Tetrahedron Lett., 1994, 35, 23; (j) M. Kunishima, K. Hioki, S. Tani and A. Kato, Tetrahedron Lett., 1994, 35, 7253; (k) D. F. Taber and R. P. Meagley, Tetrahedron Lett., 1994, 35, 7909; (l) S. Kim and C. M. Cho, Tetrahedron Lett., 1994, 35, 8405; (m) D. F. Taber, A. Sahli, H. Yu and R. P. Meagley, J. Org. Chem., 1995, 60, 6571; (n) D. F. Taber, R. P. Meagley and D. J. Doren, J. Org. Chem., 1996, 61, 5723.
16. For cyclopentene annulation via [1,5] C-H insertion of alkylidene carbene; (a) J. Wolinsky, G. W. Clark and P. C. Thorstenson, J. Org. Chem., 1976, 41, 745; (b) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251; (c) J. C. Gilbert, D. H. Giamalva and M. E. Baze, J. Org. Chem., 1985, 50, 2557; (d) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281; (e) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721; (g) M. Ochiai, K. Uemura and Y. Masaki, J. Am. Chem. Soc., 1993, 115, 2528; (h) S. Ohira, T. Moritani, T. Ida and M. Yamato, J. Chem. Soc., Chem. Commun., 1993, 1299; (i) R. R. Tykwinski, P. J. Stang and N. E. Persky, Tetrahedron Lett., 1994, 35, 23; (j) M. Kunishima, K. Hioki, S. Tani and A. Kato, Tetrahedron Lett., 1994, 35, 7253; (k) D. F. Taber and R. P. Meagley, Tetrahedron Lett., 1994, 35, 7909; (l) S. Kim and C. M. Cho, Tetrahedron Lett., 1994, 35, 8405; (m) D. F. Taber, A. Sahli, H. Yu and R. P. Meagley, J. Org. Chem., 1995, 60, 6571; (n) D. F. Taber, R. P. Meagley and D. J. Doren, J. Org. Chem., 1996, 61, 5723.
17. For cyclopentene annulation via [1,5] C-H insertion of alkylidene carbene; (a) J. Wolinsky, G. W. Clark and P. C. Thorstenson, J. Org. Chem., 1976, 41, 745; (b) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251; (c) J. C. Gilbert, D. H. Giamalva and M. E. Baze, J. Org. Chem., 1985, 50, 2557; (d) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281; (e) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721; (g) M. Ochiai, K. Uemura and Y. Masaki, J. Am. Chem. Soc., 1993, 115, 2528; (h) S. Ohira, T. Moritani, T. Ida and M. Yamato, J. Chem. Soc., Chem. Commun., 1993, 1299; (i) R. R. Tykwinski, P. J. Stang and N. E. Persky, Tetrahedron Lett., 1994, 35, 23; (j) M. Kunishima, K. Hioki, S. Tani and A. Kato, Tetrahedron Lett., 1994, 35, 7253; (k) D. F. Taber and R. P. Meagley, Tetrahedron Lett., 1994, 35, 7909; (l) S. Kim and C. M. Cho, Tetrahedron Lett., 1994, 35, 8405; (m) D. F. Taber, A. Sahli, H. Yu and R. P. Meagley, J. Org. Chem., 1995, 60, 6571; (n) D. F. Taber, R. P. Meagley and D. J. Doren, J. Org. Chem., 1996, 61, 5723.
18. For cyclopentene annulation via [1,5] C-H insertion of alkylidene carbene; (a) J. Wolinsky, G. W. Clark and P. C. Thorstenson, J. Org. Chem., 1976, 41, 745; (b) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251; (c) J. C. Gilbert, D. H. Giamalva and M. E. Baze, J. Org. Chem., 1985, 50, 2557; (d) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281; (e) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721; (g) M. Ochiai, K. Uemura and Y. Masaki, J. Am. Chem. Soc., 1993, 115, 2528; (h) S. Ohira, T. Moritani, T. Ida and M. Yamato, J. Chem. Soc., Chem. Commun., 1993, 1299; (i) R. R. Tykwinski, P. J. Stang and N. E. Persky, Tetrahedron Lett., 1994, 35, 23; (j) M. Kunishima, K. Hioki, S. Tani and A. Kato, Tetrahedron Lett., 1994, 35, 7253; (k) D. F. Taber and R. P. Meagley, Tetrahedron Lett., 1994, 35, 7909; (l) S. Kim and C. M. Cho, Tetrahedron Lett., 1994, 35, 8405; (m) D. F. Taber, A. Sahli, H. Yu and R. P. Meagley, J. Org. Chem., 1995, 60, 6571; (n) D. F. Taber, R. P. Meagley and D. J. Doren, J. Org. Chem., 1996, 61, 5723.
19. For cyclopentene annulation via [1,5] C-H insertion of alkylidene carbene; (a) J. Wolinsky, G. W. Clark and P. C. Thorstenson, J. Org. Chem., 1976, 41, 745; (b) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251; (c) J. C. Gilbert, D. H. Giamalva and M. E. Baze, J. Org. Chem., 1985, 50, 2557; (d) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281; (e) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721; (g) M. Ochiai, K. Uemura and Y. Masaki, J. Am. Chem. Soc., 1993, 115, 2528; (h) S. Ohira, T. Moritani, T. Ida and M. Yamato, J. Chem. Soc., Chem. Commun., 1993, 1299; (i) R. R. Tykwinski, P. J. Stang and N. E. Persky, Tetrahedron Lett., 1994, 35, 23; (j) M. Kunishima, K. Hioki, S. Tani and A. Kato, Tetrahedron Lett., 1994, 35, 7253; (k) D. F. Taber and R. P. Meagley, Tetrahedron Lett., 1994, 35, 7909; (l) S. Kim and C. M. Cho, Tetrahedron Lett., 1994, 35, 8405; (m) D. F. Taber, A. Sahli, H. Yu and R. P. Meagley, J. Org. Chem., 1995, 60, 6571; (n) D. F. Taber, R. P. Meagley and D. J. Doren, J. Org. Chem., 1996, 61, 5723.
20. For cyclopentene annulation via [1,5] C-H insertion of alkylidene carbene; (a) J. Wolinsky, G. W. Clark and P. C. Thorstenson, J. Org. Chem., 1976, 41, 745; (b) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251; (c) J. C. Gilbert, D. H. Giamalva and M. E. Baze, J. Org. Chem., 1985, 50, 2557; (d) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281; (e) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721; (g) M. Ochiai, K. Uemura and Y. Masaki, J. Am. Chem. Soc., 1993, 115, 2528; (h) S. Ohira, T. Moritani, T. Ida and M. Yamato, J. Chem. Soc., Chem. Commun., 1993, 1299; (i) R. R. Tykwinski, P. J. Stang and N. E. Persky, Tetrahedron Lett., 1994, 35, 23; (j) M. Kunishima, K. Hioki, S. Tani and A. Kato, Tetrahedron Lett., 1994, 35, 7253; (k) D. F. Taber and R. P. Meagley, Tetrahedron Lett., 1994, 35, 7909; (l) S. Kim and C. M. Cho, Tetrahedron Lett., 1994, 35, 8405; (m) D. F. Taber, A. Sahli, H. Yu and R. P. Meagley, J. Org. Chem., 1995, 60, 6571; (n) D. F. Taber, R. P. Meagley and D. J. Doren, J. Org. Chem., 1996, 61, 5723.
21. For cyclopentene annulation via [1,5] C-H insertion of alkylidene carbene; (a) J. Wolinsky, G. W. Clark and P. C. Thorstenson, J. Org. Chem., 1976, 41, 745; (b) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251; (c) J. C. Gilbert, D. H. Giamalva and M. E. Baze, J. Org. Chem., 1985, 50, 2557; (d) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281; (e) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721; (g) M. Ochiai, K. Uemura and Y. Masaki, J. Am. Chem. Soc., 1993, 115, 2528; (h) S. Ohira, T. Moritani, T. Ida and M. Yamato, J. Chem. Soc., Chem. Commun., 1993, 1299; (i) R. R. Tykwinski, P. J. Stang and N. E. Persky, Tetrahedron Lett., 1994, 35, 23; (j) M. Kunishima, K. Hioki, S. Tani and A. Kato, Tetrahedron Lett., 1994, 35, 7253; (k) D. F. Taber and R. P. Meagley, Tetrahedron Lett., 1994, 35, 7909; (l) S. Kim and C. M. Cho, Tetrahedron Lett., 1994, 35, 8405; (m) D. F. Taber, A. Sahli, H. Yu and R. P. Meagley, J. Org. Chem., 1995, 60, 6571; (n) D. F. Taber, R. P. Meagley and D. J. Doren, J. Org. Chem., 1996, 61, 5723.
22. For cyclopentene annulation via [1,5] C-H insertion of alkylidene carbene; (a) J. Wolinsky, G. W. Clark and P. C. Thorstenson, J. Org. Chem., 1976, 41, 745; (b) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251; (c) J. C. Gilbert, D. H. Giamalva and M. E. Baze, J. Org. Chem., 1985, 50, 2557; (d) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281; (e) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721; (g) M. Ochiai, K. Uemura and Y. Masaki, J. Am. Chem. Soc., 1993, 115, 2528; (h) S. Ohira, T. Moritani, T. Ida and M. Yamato, J. Chem. Soc., Chem. Commun., 1993, 1299; (i) R. R. Tykwinski, P. J. Stang and N. E. Persky, Tetrahedron Lett., 1994, 35, 23; (j) M. Kunishima, K. Hioki, S. Tani and A. Kato, Tetrahedron Lett., 1994, 35, 7253; (k) D. F. Taber and R. P. Meagley, Tetrahedron Lett., 1994, 35, 7909; (l) S. Kim and C. M. Cho, Tetrahedron Lett., 1994, 35, 8405; (m) D. F. Taber, A. Sahli, H. Yu and R. P. Meagley, J. Org. Chem., 1995, 60, 6571; (n) D. F. Taber, R. P. Meagley and D. J. Doren, J. Org. Chem., 1996, 61, 5723.
23. For cyclopentene annulation via [1,5] C-H insertion of alkylidene carbene; (a) J. Wolinsky, G. W. Clark and P. C. Thorstenson, J. Org. Chem., 1976, 41, 745; (b) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251; (c) J. C. Gilbert, D. H. Giamalva and M. E. Baze, J. Org. Chem., 1985, 50, 2557; (d) M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro and E. Fujita, J. Am. Chem. Soc., 1986, 108, 8281; (e) M. Ochiai, M. Kunishima, S. Tani and Y. Nagao, J. Am. Chem. Soc., 1991, 113, 3135; (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721; (g) M. Ochiai, K. Uemura and Y. Masaki, J. Am. Chem. Soc., 1993, 115, 2528; (h) S. Ohira, T. Moritani, T. Ida and M. Yamato, J. Chem. Soc., Chem. Commun., 1993, 1299; (i) R. R. Tykwinski, P. J. Stang and N. E. Persky, Tetrahedron Lett., 1994, 35, 23; (j) M. Kunishima, K. Hioki, S. Tani and A. Kato, Tetrahedron Lett., 1994, 35, 7253; (k) D. F. Taber and R. P. Meagley, Tetrahedron Lett., 1994, 35, 7909; (l) S. Kim and C. M. Cho, Tetrahedron Lett., 1994, 35, 8405; (m) D. F. Taber, A. Sahli, H. Yu and R. P. Meagley, J. Org. Chem., 1995, 60, 6571; (n) D. F. Taber, R. P. Meagley and D. J. Doren, J. Org. Chem., 1996, 61, 5723.
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