Electrocyclic reactions of 13-cis-retinal schiff bases

Journal of the American Chemical Society

Volumn 110, Issue 13, 1988, Pages 4462-4464

  Okamura, William H ^a   de Lera, Angel R ^a   Reischl, Wolfgang ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845280286     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00221a084     Document Type: Article

References (10)

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2. Harbison, G. S.; Smith, S. O.; Pardoen, J. A.; Winkel, C.; Lugtenburg, J.; Herzfeld, J.; Mathies, R.; Griffin, R. G. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 1706. (b) Smith, S. O.; Myers, A. B.; Pardoen, J. A.; Winkel, C.; Mulder, P. P. J.; Lugtenburg, J.; Mathies, R. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 2055. (c) Gerwert, K.; Siebert, F. The EMBO J. 1986, 5, 805. (d) Tavan, P.; Schulten, K. Biophys. J. 1986, 50, 81. (e) Eisenstein, L.; Lin, S.-L.; Dollinger, G.; Odashima, K.; Termini, J.; Konno, K.; Ding, W.-D.; Nakanishi, K. J. Am. Chem. Soc. 1987, 109, 6860. (f) Smith, S. O.; Hornung, L; van der Steen, R.; Pardoen, J. A.; Braiman, M. S.; Lugtenburg, J.; Mathies, R. A. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 967.
3. In addition to ref 2b-f, see: (a) Schaffer, A. M.; Waddell, W. H.; Becker, R. S. J. Am. Chem. Soc. 1974, 96, 2063. (b) Cookingham, R. E.; Lewis, A.; Lemley, A. T. Biochemistry 1978, 17, 4699. (c) Marcus, A.; Lewis, A. Biochemistry 1978, 17, 4722. (d) Rothschild, K. J.; Roepe, P.; Lugtenburg, J.; Pardoen, J. A. Biochemistry 1984, 23, 6103. (e) Wingen, U.; Simon, L.; Klein, M.; Buss, V. Angew. Chem., Int. Ed. Engl. 1985, 24, 761. (f) López-Garriga, J. J.; Babcock, G. T.; Harrison, J. F. J. Am. Chem. Soc. 1986, 108, 7131. (g) Freedman, K. A.; Becker, R. S. J. Am. Chem. Soc. 1986, 108, 1245. (h) Seltzer, S.; Zuckermann, R. J. Am. Chem. Soc. 1985, 107, 5523. (i) Seltzer, S. J. Am. Chem. Soc. 1987, 109, 1627. (j) Baasov, T.; Friedman, N.; Sheves, M. Biochemistry 1987, 26, 3210. In addition to ref 2a, for recent NMR studies see: (k) Sheves, M.; Baasov, T. J. Am. Chem. Soc. 1984, 106, 6840. (l) Birge, R. R.; Murray, L. P.; Zidovetzki, R.; Knapp,. M. J. Am. Chem. Soc. 1987, 109, 2090. (m) Childs, R. F.; Shaw, G. S.; Wasylishen, R. E. J. Am. Chem. Soc. 1987, 109, 5362.
4. de Lera, A. R.; Okamura, W. H. Tetrahedron Lett. 1987, 28, 2921. (b) Chandraratna, R. A. S.; Bayerque, A. L.; Okamura, W. H. J. Am. Chem. Soc. 1983, 105, 3588. (c) Chandraratna, R. A. S.; Okamura, W. H. Tetrahedron Lett. 1984, 25, 1003. (d) Ernst, L.; Hopf, H.; Krause, N. J. Org. Chem. 1987, 52, 398.
5. Marvell, E. N. Thermal Electrocyclic Reactions; Academic: New York, 1980. (b) Marvell, E. N.; Caple, G.; Schatz, B.; Pippin, W. Tetrahedron 1973, 29, 3781. (c) Marvell, E. N.; Seubert, J. J. Am. Chem. Soc. 1967, 89, 3377. (d) Huisgen, R.; Dahmen, A.; Huber, H. J. Am. Chem. Soc. 1967, 89, 7130.
6. Ghirlando, R.; Berman, E.; Baasov, T.; Sheves, M. Magn. Reson. Chem. 1987, 25, 21. (b) Lukton, R.; Rando, R. R. J. Am. Chem. Soc. 1984, 106, 4525. (c) Pattaroni, C.; Lauterwein, J. Helv. Chim. Acta 1981, 64, 1969. (d) Cossette, D.; Vocelle, D. Can. J. Chem. 1987, 65, 661, 1576. (e) Sharma, G. M.; Roels, O. A. J. Org. Chem. 1973, 38, 3648.
7. Schiess, P.; Chia, H. L.; Ringele, P. Tetrahedron Lett. 1972, 313. (b) See also: Baran, J.; Mayr, H. J. Am. Chem. Soc. 1987, 109, 6519. For an analogous transformation leading to dihydropyrans, see ref 5 and, for example: (c) Kluge, A. F.; Lillya, C. P. J. Am. Chem. Soc. 1971, 93, 4458; J. Org. Chem. 1971, 36, 1988.
8. Cheng, Y.-S.; Lupo, A. T., Jr.; Fowler, F. W. J. Am. Chem. Soc. 1983, 105, 7696. (b) Wyle, M. J.; Fowler, F. W. J. Org. Chem. 1984, 49, 4025.
9. LA exists in the 12-s-cis conformation. Besides ref 3g, see also: (a) Muradin-Szweykowska, M.; Broek, A. D.; Lugtenburg, J.; van der Bend, R. L.; van Dijck, P. W. M. Recl. Trav. Chim. Pays-Bas 1983, 102, 42. (b) Muradin-Szweykowska, M.; Peters, A. J. M.; Lugtenburg, J. Reel. Trav. Chim. Pays-Bas 1984, 103, 105.
10. Findlay, J. B. C.; Pappin, D. J. C. Biochem. J. 1986, 238, 625.