Photocyclization-fragmentation route to di- and triquinanes: Stereocontrolled asymmetric synthesis of (-)-isocomene

Pure and Applied Chemistry

Volumn 68, Issue 3, 1996, Pages 675-678

  Rawal, Viresh H ^a   Eschbach, Andrew ^a   Dufour, Claire ^a   Iwasa, Seiji ^a  

^a OHIO STATE UNIVERSITY   (United States)

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EID: 0011985576     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199668030675     Document Type: Article

References (29)

1. Rawal, V. H.; Dufour, C. J. Am. Chem. Soc. 1994, 116, 2613.
2. Rawal, V. H.; Dufour, C.; Iwasa, S. Tetrahedron Lett. 1995, 36, 19.
3. Rawal, V. H.; Dufour, C.; Eschbach, A. J. Chem. Soc., Chem. Commun. 1994, 1797.
4. Isolation: (a) Zalkow, L. H.; Harris, R. N., III; Van Derveer, D.; Bertrand, J. A. J. Chem. Soc., Chem. Commun. 1977, 456. (b) Zalkow, L. H.; Harris, R. N., III; Burke, N. I. J. Nat. Prod. 1979, 42, 96. (c) Bohlmann, F.; Le Van, N.; Pickardt, J. Chem. Ber. 1977, 110, 3777.
5. Isolation: (a) Zalkow, L. H.; Harris, R. N., III; Van Derveer, D.; Bertrand, J. A. J. Chem. Soc., Chem. Commun. 1977, 456. (b) Zalkow, L. H.; Harris, R. N., III; Burke, N. I. J. Nat. Prod. 1979, 42, 96. (c) Bohlmann, F.; Le Van, N.; Pickardt, J. Chem. Ber. 1977, 110, 3777.
6. Isolation: (a) Zalkow, L. H.; Harris, R. N., III; Van Derveer, D.; Bertrand, J. A. J. Chem. Soc., Chem. Commun. 1977, 456. (b) Zalkow, L. H.; Harris, R. N., III; Burke, N. I. J. Nat. Prod. 1979, 42, 96. (c) Bohlmann, F.; Le Van, N.; Pickardt, J. Chem. Ber. 1977, 110, 3777.
7. Several syntheses of racemic isocomene have been reported: (a) Oppolzer, W.; Battig, K.; Hudlicky, T. Helv. Chim. Acta 1979, 62, 1493. (b) Oppolzer, W.; Battig, K.; Hudlicky, T. Tetrahedron 1981, 37, 4359. (c) Paquette, L. A.; Han, Y. K. J. Am. Chem. Soc. 1981, 103, 1835. (d) Paquette, L. A.; Han, Y. K. J. Org. Chem. 1979, 44, 4014. (e) Pirrung, M. C. J. Am. Chem. Soc. 1979, 101, 7130. (f) Pirrung, M. C. J. Am. Chem. Soc. 1981, 103, 82. (g) Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103. (h) Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445. (i) Wenkert, E.; Arrhenius, T. S. J. Am. Chem. Soc. 1983, 105, 2030. (j) Ranu, B. C.; Kavka, M.; Higgs, L. A.; Hudlicky, T. Tetrahedron Lett. 1984, 25, 2447. (k) Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. (l) Manzardo, G. G. G.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 659. (m) Fitjer, L.; Kanschik, A.; Majewski, M. Tetrahedron Lett. 1988, 29, 5525.
8. Several syntheses of racemic isocomene have been reported: (a) Oppolzer, W.; Battig, K.; Hudlicky, T. Helv. Chim. Acta 1979, 62, 1493. (b) Oppolzer, W.; Battig, K.; Hudlicky, T. Tetrahedron 1981, 37, 4359. (c) Paquette, L. A.; Han, Y. K. J. Am. Chem. Soc. 1981, 103, 1835. (d) Paquette, L. A.; Han, Y. K. J. Org. Chem. 1979, 44, 4014. (e) Pirrung, M. C. J. Am. Chem. Soc. 1979, 101, 7130. (f) Pirrung, M. C. J. Am. Chem. Soc. 1981, 103, 82. (g) Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103. (h) Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445. (i) Wenkert, E.; Arrhenius, T. S. J. Am. Chem. Soc. 1983, 105, 2030. (j) Ranu, B. C.; Kavka, M.; Higgs, L. A.; Hudlicky, T. Tetrahedron Lett. 1984, 25, 2447. (k) Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. (l) Manzardo, G. G. G.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 659. (m) Fitjer, L.; Kanschik, A.; Majewski, M. Tetrahedron Lett. 1988, 29, 5525.
9. Several syntheses of racemic isocomene have been reported: (a) Oppolzer, W.; Battig, K.; Hudlicky, T. Helv. Chim. Acta 1979, 62, 1493. (b) Oppolzer, W.; Battig, K.; Hudlicky, T. Tetrahedron 1981, 37, 4359. (c) Paquette, L. A.; Han, Y. K. J. Am. Chem. Soc. 1981, 103, 1835. (d) Paquette, L. A.; Han, Y. K. J. Org. Chem. 1979, 44, 4014. (e) Pirrung, M. C. J. Am. Chem. Soc. 1979, 101, 7130. (f) Pirrung, M. C. J. Am. Chem. Soc. 1981, 103, 82. (g) Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103. (h) Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445. (i) Wenkert, E.; Arrhenius, T. S. J. Am. Chem. Soc. 1983, 105, 2030. (j) Ranu, B. C.; Kavka, M.; Higgs, L. A.; Hudlicky, T. Tetrahedron Lett. 1984, 25, 2447. (k) Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. (l) Manzardo, G. G. G.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 659. (m) Fitjer, L.; Kanschik, A.; Majewski, M. Tetrahedron Lett. 1988, 29, 5525.
10. Several syntheses of racemic isocomene have been reported: (a) Oppolzer, W.; Battig, K.; Hudlicky, T. Helv. Chim. Acta 1979, 62, 1493. (b) Oppolzer, W.; Battig, K.; Hudlicky, T. Tetrahedron 1981, 37, 4359. (c) Paquette, L. A.; Han, Y. K. J. Am. Chem. Soc. 1981, 103, 1835. (d) Paquette, L. A.; Han, Y. K. J. Org. Chem. 1979, 44, 4014. (e) Pirrung, M. C. J. Am. Chem. Soc. 1979, 101, 7130. (f) Pirrung, M. C. J. Am. Chem. Soc. 1981, 103, 82. (g) Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103. (h) Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445. (i) Wenkert, E.; Arrhenius, T. S. J. Am. Chem. Soc. 1983, 105, 2030. (j) Ranu, B. C.; Kavka, M.; Higgs, L. A.; Hudlicky, T. Tetrahedron Lett. 1984, 25, 2447. (k) Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. (l) Manzardo, G. G. G.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 659. (m) Fitjer, L.; Kanschik, A.; Majewski, M. Tetrahedron Lett. 1988, 29, 5525.
11. Several syntheses of racemic isocomene have been reported: (a) Oppolzer, W.; Battig, K.; Hudlicky, T. Helv. Chim. Acta 1979, 62, 1493. (b) Oppolzer, W.; Battig, K.; Hudlicky, T. Tetrahedron 1981, 37, 4359. (c) Paquette, L. A.; Han, Y. K. J. Am. Chem. Soc. 1981, 103, 1835. (d) Paquette, L. A.; Han, Y. K. J. Org. Chem. 1979, 44, 4014. (e) Pirrung, M. C. J. Am. Chem. Soc. 1979, 101, 7130. (f) Pirrung, M. C. J. Am. Chem. Soc. 1981, 103, 82. (g) Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103. (h) Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445. (i) Wenkert, E.; Arrhenius, T. S. J. Am. Chem. Soc. 1983, 105, 2030. (j) Ranu, B. C.; Kavka, M.; Higgs, L. A.; Hudlicky, T. Tetrahedron Lett. 1984, 25, 2447. (k) Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. (l) Manzardo, G. G. G.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 659. (m) Fitjer, L.; Kanschik, A.; Majewski, M. Tetrahedron Lett. 1988, 29, 5525.
12. Several syntheses of racemic isocomene have been reported: (a) Oppolzer, W.; Battig, K.; Hudlicky, T. Helv. Chim. Acta 1979, 62, 1493. (b) Oppolzer, W.; Battig, K.; Hudlicky, T. Tetrahedron 1981, 37, 4359. (c) Paquette, L. A.; Han, Y. K. J. Am. Chem. Soc. 1981, 103, 1835. (d) Paquette, L. A.; Han, Y. K. J. Org. Chem. 1979, 44, 4014. (e) Pirrung, M. C. J. Am. Chem. Soc. 1979, 101, 7130. (f) Pirrung, M. C. J. Am. Chem. Soc. 1981, 103, 82. (g) Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103. (h) Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445. (i) Wenkert, E.; Arrhenius, T. S. J. Am. Chem. Soc. 1983, 105, 2030. (j) Ranu, B. C.; Kavka, M.; Higgs, L. A.; Hudlicky, T. Tetrahedron Lett. 1984, 25, 2447. (k) Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. (l) Manzardo, G. G. G.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 659. (m) Fitjer, L.; Kanschik, A.; Majewski, M. Tetrahedron Lett. 1988, 29, 5525.
13. Several syntheses of racemic isocomene have been reported: (a) Oppolzer, W.; Battig, K.; Hudlicky, T. Helv. Chim. Acta 1979, 62, 1493. (b) Oppolzer, W.; Battig, K.; Hudlicky, T. Tetrahedron 1981, 37, 4359. (c) Paquette, L. A.; Han, Y. K. J. Am. Chem. Soc. 1981, 103, 1835. (d) Paquette, L. A.; Han, Y. K. J. Org. Chem. 1979, 44, 4014. (e) Pirrung, M. C. J. Am. Chem. Soc. 1979, 101, 7130. (f) Pirrung, M. C. J. Am. Chem. Soc. 1981, 103, 82. (g) Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103. (h) Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445. (i) Wenkert, E.; Arrhenius, T. S. J. Am. Chem. Soc. 1983, 105, 2030. (j) Ranu, B. C.; Kavka, M.; Higgs, L. A.; Hudlicky, T. Tetrahedron Lett. 1984, 25, 2447. (k) Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. (l) Manzardo, G. G. G.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 659. (m) Fitjer, L.; Kanschik, A.; Majewski, M. Tetrahedron Lett. 1988, 29, 5525.
14. Several syntheses of racemic isocomene have been reported: (a) Oppolzer, W.; Battig, K.; Hudlicky, T. Helv. Chim. Acta 1979, 62, 1493. (b) Oppolzer, W.; Battig, K.; Hudlicky, T. Tetrahedron 1981, 37, 4359. (c) Paquette, L. A.; Han, Y. K. J. Am. Chem. Soc. 1981, 103, 1835. (d) Paquette, L. A.; Han, Y. K. J. Org. Chem. 1979, 44, 4014. (e) Pirrung, M. C. J. Am. Chem. Soc. 1979, 101, 7130. (f) Pirrung, M. C. J. Am. Chem. Soc. 1981, 103, 82. (g) Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103. (h) Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445. (i) Wenkert, E.; Arrhenius, T. S. J. Am. Chem. Soc. 1983, 105, 2030. (j) Ranu, B. C.; Kavka, M.; Higgs, L. A.; Hudlicky, T. Tetrahedron Lett. 1984, 25, 2447. (k) Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. (l) Manzardo, G. G. G.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 659. (m) Fitjer, L.; Kanschik, A.; Majewski, M. Tetrahedron Lett. 1988, 29, 5525.
15. Several syntheses of racemic isocomene have been reported: (a) Oppolzer, W.; Battig, K.; Hudlicky, T. Helv. Chim. Acta 1979, 62, 1493. (b) Oppolzer, W.; Battig, K.; Hudlicky, T. Tetrahedron 1981, 37, 4359. (c) Paquette, L. A.; Han, Y. K. J. Am. Chem. Soc. 1981, 103, 1835. (d) Paquette, L. A.; Han, Y. K. J. Org. Chem. 1979, 44, 4014. (e) Pirrung, M. C. J. Am. Chem. Soc. 1979, 101, 7130. (f) Pirrung, M. C. J. Am. Chem. Soc. 1981, 103, 82. (g) Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103. (h) Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445. (i) Wenkert, E.; Arrhenius, T. S. J. Am. Chem. Soc. 1983, 105, 2030. (j) Ranu, B. C.; Kavka, M.; Higgs, L. A.; Hudlicky, T. Tetrahedron Lett. 1984, 25, 2447. (k) Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. (l) Manzardo, G. G. G.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 659. (m) Fitjer, L.; Kanschik, A.; Majewski, M. Tetrahedron Lett. 1988, 29, 5525.
16. Several syntheses of racemic isocomene have been reported: (a) Oppolzer, W.; Battig, K.; Hudlicky, T. Helv. Chim. Acta 1979, 62, 1493. (b) Oppolzer, W.; Battig, K.; Hudlicky, T. Tetrahedron 1981, 37, 4359. (c) Paquette, L. A.; Han, Y. K. J. Am. Chem. Soc. 1981, 103, 1835. (d) Paquette, L. A.; Han, Y. K. J. Org. Chem. 1979, 44, 4014. (e) Pirrung, M. C. J. Am. Chem. Soc. 1979, 101, 7130. (f) Pirrung, M. C. J. Am. Chem. Soc. 1981, 103, 82. (g) Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103. (h) Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445. (i) Wenkert, E.; Arrhenius, T. S. J. Am. Chem. Soc. 1983, 105, 2030. (j) Ranu, B. C.; Kavka, M.; Higgs, L. A.; Hudlicky, T. Tetrahedron Lett. 1984, 25, 2447. (k) Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. (l) Manzardo, G. G. G.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 659. (m) Fitjer, L.; Kanschik, A.; Majewski, M. Tetrahedron Lett. 1988, 29, 5525.
17. Several syntheses of racemic isocomene have been reported: (a) Oppolzer, W.; Battig, K.; Hudlicky, T. Helv. Chim. Acta 1979, 62, 1493. (b) Oppolzer, W.; Battig, K.; Hudlicky, T. Tetrahedron 1981, 37, 4359. (c) Paquette, L. A.; Han, Y. K. J. Am. Chem. Soc. 1981, 103, 1835. (d) Paquette, L. A.; Han, Y. K. J. Org. Chem. 1979, 44, 4014. (e) Pirrung, M. C. J. Am. Chem. Soc. 1979, 101, 7130. (f) Pirrung, M. C. J. Am. Chem. Soc. 1981, 103, 82. (g) Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103. (h) Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445. (i) Wenkert, E.; Arrhenius, T. S. J. Am. Chem. Soc. 1983, 105, 2030. (j) Ranu, B. C.; Kavka, M.; Higgs, L. A.; Hudlicky, T. Tetrahedron Lett. 1984, 25, 2447. (k) Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. (l) Manzardo, G. G. G.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 659. (m) Fitjer, L.; Kanschik, A.; Majewski, M. Tetrahedron Lett. 1988, 29, 5525.
18. Several syntheses of racemic isocomene have been reported: (a) Oppolzer, W.; Battig, K.; Hudlicky, T. Helv. Chim. Acta 1979, 62, 1493. (b) Oppolzer, W.; Battig, K.; Hudlicky, T. Tetrahedron 1981, 37, 4359. (c) Paquette, L. A.; Han, Y. K. J. Am. Chem. Soc. 1981, 103, 1835. (d) Paquette, L. A.; Han, Y. K. J. Org. Chem. 1979, 44, 4014. (e) Pirrung, M. C. J. Am. Chem. Soc. 1979, 101, 7130. (f) Pirrung, M. C. J. Am. Chem. Soc. 1981, 103, 82. (g) Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103. (h) Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445. (i) Wenkert, E.; Arrhenius, T. S. J. Am. Chem. Soc. 1983, 105, 2030. (j) Ranu, B. C.; Kavka, M.; Higgs, L. A.; Hudlicky, T. Tetrahedron Lett. 1984, 25, 2447. (k) Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. (l) Manzardo, G. G. G.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 659. (m) Fitjer, L.; Kanschik, A.; Majewski, M. Tetrahedron Lett. 1988, 29, 5525.
19. Several syntheses of racemic isocomene have been reported: (a) Oppolzer, W.; Battig, K.; Hudlicky, T. Helv. Chim. Acta 1979, 62, 1493. (b) Oppolzer, W.; Battig, K.; Hudlicky, T. Tetrahedron 1981, 37, 4359. (c) Paquette, L. A.; Han, Y. K. J. Am. Chem. Soc. 1981, 103, 1835. (d) Paquette, L. A.; Han, Y. K. J. Org. Chem. 1979, 44, 4014. (e) Pirrung, M. C. J. Am. Chem. Soc. 1979, 101, 7130. (f) Pirrung, M. C. J. Am. Chem. Soc. 1981, 103, 82. (g) Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103. (h) Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445. (i) Wenkert, E.; Arrhenius, T. S. J. Am. Chem. Soc. 1983, 105, 2030. (j) Ranu, B. C.; Kavka, M.; Higgs, L. A.; Hudlicky, T. Tetrahedron Lett. 1984, 25, 2447. (k) Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. (l) Manzardo, G. G. G.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 659. (m) Fitjer, L.; Kanschik, A.; Majewski, M. Tetrahedron Lett. 1988, 29, 5525.
20. During the course of our work, Fitjer deduced the absolute configuration of isocomene by correlating the chiral GC of the natural material with the products of stereospecific rearrangements of an optically active dispirane: Fitjer, L; Monzó-Oltra, H. J. Org. Chem. 1993, 58, 6171.
21. Helmchen, Tetrahedron Lett. 1985, 26, 3095.
22. The minor diastereomer has been assigned tentatively as the other endo diastereomer.
23. Krapcho, A. P.; Dundulis, E. A. J. Org. Chem. 1980, 45, 3236.
24. Sauers, R. R.; Schinski, W.; Sickles, B. In Organic Photochemical Synthesis; Srinivasan, R.; Roberts, T. D., Eds.; Wiley: New York, 1971; p 76. See also ref 1.
25. Cooke, M. P, Jr. J. Org. Chem. 1992, 57, 1495, and references cited therein.
26. Comins, D. L.; Delhangi, A. Tetrahedron Lett. 1992, 33, 6299.
27. (a) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313.
28. (b) Review: Scott, W. J.; McMurry, J. E. Acc. Chem. Res. 1988, 21, 47.
29. The spectral data of our homochiral isocomene were identical with the racemic material (ref. 3). The slight difference in the optical rotation may be due to the small quantity of the material used for the rotation (84 mg) or to the difference in the concentration of the sample.