Efficient Construction of Bi- and Tricyclic Cyclooctanoid Systems via Crossed [4+4]-Photocycloadditions of Pyran-2-ones

Synlett

Volumn 1996, Issue 12, 1996, Pages 1173-1175

  Chase, Charles E ^a   Bender, John A ^a   West, F G ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002831435     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5717     Document Type: Article

References (25)

1. Presented in preliminary form: West, F. G.; Chase, C. E.; Bender, J. A. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA, March 1994; American Chemical Society: Washington, DC, 1994; ORGN 482.
2. Review: Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757.
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6. [6+2]: (a) Feldman, K. S.; Wu, M. J.; Rotella, D. P. J. Am. Chem. Soc. 1990, 112, 8490. (b) Pirrung, M. C. J. Org. Chem. 1987, 52, 1635. (c) Wagner, P. J.; Sakamoto, M.; Madkour, A. E. J. Am. Chem. Soc. 1992, 114, 7298. [4+3]: (d) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (e) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. [4+4]: (f) Sieburth, S. McN.; Heil, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (g) Sieburth, S. McN.; Ravindran, K. Tetrahedron Lett. 1994, 35, 3861. (h) Sieburth, S. McN.; Joshi, P. V. J. Org. Chem. 1993, 58, 1661. (i) West, F. G.; Chase, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 3794.
7. [6+2]: (a) Feldman, K. S.; Wu, M. J.; Rotella, D. P. J. Am. Chem. Soc. 1990, 112, 8490. (b) Pirrung, M. C. J. Org. Chem. 1987, 52, 1635. (c) Wagner, P. J.; Sakamoto, M.; Madkour, A. E. J. Am. Chem. Soc. 1992, 114, 7298. [4+3]: (d) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (e) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. [4+4]: (f) Sieburth, S. McN.; Heil, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (g) Sieburth, S. McN.; Ravindran, K. Tetrahedron Lett. 1994, 35, 3861. (h) Sieburth, S. McN.; Joshi, P. V. J. Org. Chem. 1993, 58, 1661. (i) West, F. G.; Chase, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 3794.
8. [6+2]: (a) Feldman, K. S.; Wu, M. J.; Rotella, D. P. J. Am. Chem. Soc. 1990, 112, 8490. (b) Pirrung, M. C. J. Org. Chem. 1987, 52, 1635. (c) Wagner, P. J.; Sakamoto, M.; Madkour, A. E. J. Am. Chem. Soc. 1992, 114, 7298. [4+3]: (d) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (e) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. [4+4]: (f) Sieburth, S. McN.; Heil, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (g) Sieburth, S. McN.; Ravindran, K. Tetrahedron Lett. 1994, 35, 3861. (h) Sieburth, S. McN.; Joshi, P. V. J. Org. Chem. 1993, 58, 1661. (i) West, F. G.; Chase, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 3794.
9. [6+2]: (a) Feldman, K. S.; Wu, M. J.; Rotella, D. P. J. Am. Chem. Soc. 1990, 112, 8490. (b) Pirrung, M. C. J. Org. Chem. 1987, 52, 1635. (c) Wagner, P. J.; Sakamoto, M.; Madkour, A. E. J. Am. Chem. Soc. 1992, 114, 7298. [4+3]: (d) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (e) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. [4+4]: (f) Sieburth, S. McN.; Heil, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (g) Sieburth, S. McN.; Ravindran, K. Tetrahedron Lett. 1994, 35, 3861. (h) Sieburth, S. McN.; Joshi, P. V. J. Org. Chem. 1993, 58, 1661. (i) West, F. G.; Chase, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 3794.
10. [6+2]: (a) Feldman, K. S.; Wu, M. J.; Rotella, D. P. J. Am. Chem. Soc. 1990, 112, 8490. (b) Pirrung, M. C. J. Org. Chem. 1987, 52, 1635. (c) Wagner, P. J.; Sakamoto, M.; Madkour, A. E. J. Am. Chem. Soc. 1992, 114, 7298. [4+3]: (d) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (e) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. [4+4]: (f) Sieburth, S. McN.; Heil, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (g) Sieburth, S. McN.; Ravindran, K. Tetrahedron Lett. 1994, 35, 3861. (h) Sieburth, S. McN.; Joshi, P. V. J. Org. Chem. 1993, 58, 1661. (i) West, F. G.; Chase, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 3794.
11. [6+2]: (a) Feldman, K. S.; Wu, M. J.; Rotella, D. P. J. Am. Chem. Soc. 1990, 112, 8490. (b) Pirrung, M. C. J. Org. Chem. 1987, 52, 1635. (c) Wagner, P. J.; Sakamoto, M.; Madkour, A. E. J. Am. Chem. Soc. 1992, 114, 7298. [4+3]: (d) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (e) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. [4+4]: (f) Sieburth, S. McN.; Heil, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (g) Sieburth, S. McN.; Ravindran, K. Tetrahedron Lett. 1994, 35, 3861. (h) Sieburth, S. McN.; Joshi, P. V. J. Org. Chem. 1993, 58, 1661. (i) West, F. G.; Chase, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 3794.
12. [6+2]: (a) Feldman, K. S.; Wu, M. J.; Rotella, D. P. J. Am. Chem. Soc. 1990, 112, 8490. (b) Pirrung, M. C. J. Org. Chem. 1987, 52, 1635. (c) Wagner, P. J.; Sakamoto, M.; Madkour, A. E. J. Am. Chem. Soc. 1992, 114, 7298. [4+3]: (d) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (e) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. [4+4]: (f) Sieburth, S. McN.; Heil, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (g) Sieburth, S. McN.; Ravindran, K. Tetrahedron Lett. 1994, 35, 3861. (h) Sieburth, S. McN.; Joshi, P. V. J. Org. Chem. 1993, 58, 1661. (i) West, F. G.; Chase, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 3794.
13. [6+2]: (a) Feldman, K. S.; Wu, M. J.; Rotella, D. P. J. Am. Chem. Soc. 1990, 112, 8490. (b) Pirrung, M. C. J. Org. Chem. 1987, 52, 1635. (c) Wagner, P. J.; Sakamoto, M.; Madkour, A. E. J. Am. Chem. Soc. 1992, 114, 7298. [4+3]: (d) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (e) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. [4+4]: (f) Sieburth, S. McN.; Heil, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (g) Sieburth, S. McN.; Ravindran, K. Tetrahedron Lett. 1994, 35, 3861. (h) Sieburth, S. McN.; Joshi, P. V. J. Org. Chem. 1993, 58, 1661. (i) West, F. G.; Chase, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 3794.
14. For a recent study of the photochemistry of pyran-2-ones bearing C-4 tethered alkenes and dienes, see: Shimo, T.; Ueda, S.; Somekawa, K. J. Heterocyclic Chem. 1995, 32, 341.
15. Breslow, R. Acc. Chem. Res. 1991, 24, 159.
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17. 2).
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20. (c) For a recent study implicating β-lactone intermediates in 2-pyrone photorearrangements, see: Chase, C. E.; Jarstfer, M. B.; Arif, A. M.; West, F. G. Tetrahedron Lett. 1995, 36, 8531.
21. 1H NMR spectra.
22. 4i led to low conversion and a 1:1 ratio of endo and exo cycloadducts. Low water solubility (ca. 9 mg/0.5 L) precluded the use of aq. LiCl.
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24. 4), filtered, and concentrated to a yellow oil. The crude product was purified by radial chromatography (silica gel, 1 mm rotor, hexanes/EtOAc 19:1) to give 5i (10 mg, 0.029 mmol, 20%), 6i (29 mg, 0.084 mmol, 58%) and 8i (2 mg, 0.006 mmol, 4%).
25. For a recently published, related approach to a 5-8-5 skeleton via an intramolecular [4+3]-cycloaddition, see: Harmata, M.; Elomari, S.; Barnes, C. L. J. Am. Chem. Soc. 1996, 118, 2860.