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7. Application to the synthesis of complex molecules

323

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84.(a) S. L. Schreiber and K. Satake, J. Am. Chem. Soc., 105, 6723 (1983).

(b)S. L. Schreiber and K. Satake, J. Am. Chem. Soc., 106, 4186 (1984).

(c)S. L. Schreiber and K. Satake, Tetrahedron Lett., 27, 2575 (1986).

85.(a) S. L. Schreiber, D. Desmaele and J. A. Porco, Jr., Tetrahedron Lett., 29, 6689 (1988).

(b)S. L. Schreiber and J. A. Porco, Jr., J. Org. Chem., 54, 4721 (1989).

86.See also: S. L. Schreiber, J. A. Porco, R. C. Hawley, and D. Desmaele, New Methods Drug Res., 3, 13 (1989).

87.A. H. Hoveyda, Ph.D. Dissertation, Yale University, 1986.

88.(a) S. Jarosz and A. Zamojski, Pol. J. Chem., 56, 433 (1982).

(b)S. Jarosz and A. Zamojski, Tetrahedron, 38, 1447 (1982).

(c)S. Jarosz and A. Zamojski, Tetrahedron, 38, 1453 (1982).

(d)T. Kozluk and A. Zamojski, Tetrahedron, 39, 805 (1983).

89.G. Jones, II, H. M. Gilow and J. Low, J. Org. Chem., 44, 2949 (1979).

90.For reviews of [4 C 4] and related higher-order cycloadditions, see:

(a)S. McN. Sieburth and N. Cunard, Tetrahedron, 52, 6251 (1996).

(b)J. H. Rigby, in Comprehensive Organic Synthesis, Vol. 5: Combining C C -Bonds (Eds. B. M. Trost and I. Fleming), Chap. 5.2, Pergamon, Oxford, 1991.

91.G. Sartori, V. Turba, A. Valvassori and M. Riva, Tetrahedron Lett., 211 (1966).

92.(a) R. Hertel, J. Mattay and J. Runsink, J. Am. Chem. Soc., 113, 657 (1991).

(b)K. Langer, J. Mattay, A. Heidbreder and M. Moller,¨ Justus Liebigs Ann. Chem., 257 (1992).

93.S. Masamune, R. T. Seidner, H. Zenda, M. Wiesel, N. Nakatsuka and G. Bigam, J. Am. Chem. Soc., 90, 5286 (1968).

94.E. Babad, D. Ginsburg and M. B. Rubin, Tetrahedron Lett., 2361 (1968).

95.A. Srikrishna and G. Sunderbabu, J. Org. Chem., 52, 5037 (1987).

96.H. Shigemori, M. -A. Bae, K. Yazawa, T. Sasaki and J. Kobayashi, J. Org. Chem., 57, 4317 (1992).

97.(a) J. Fritzsche, J. Prakt. Chem., 101, 333 (1867).

(b)Review: H. -D. Becker, Chem. Rev., 93, 145 (1993).

98.J. S. Bradshaw and G. S. Hammond, J. Am. Chem. Soc., 85, 3953 (1963).

99.(a) L. J. Sharp, IV and G. S. Hammond, Mol. Photochem., 2, 225 (1970).

(b)Y. Nakamura, T. Kato and Y. Morita, J. Chem. Soc., Perkin Trans. 1, 1187 (1982).

100.(a) E. C. Taylor and R. O. Kan, J. Am. Chem. Soc., 85, 776 (1963).

(b)E. C. Taylor and G. Spence, in Organic Photochemical Synthesis (Ed. R. Srinivasan), Vol. 1, Wiley, New York, 1971, p. 46.

101.For representative examples of crossed photochemical [4 C 4]-cycloadditions, see:

(a)A. Gilbert and O. Griffiths, J. Chem. Soc., Perkin Trans. 1, 1379 (1993).

(b)E. Sato, Y. Ikeda and Y. Kanaoka, Justus Liebigs Ann. Chem., 781 (1989).

(c)J. Saltiel, R. Dabestani, K. S. Schanze, D. Trojan, D. E. Townsend and V. L. Goedken, J. Am. Chem. Soc., 108, 2674 (1986).

(d)N. C. Yang and M. G. Horner, Tetrahedron Lett., 27, 543 (1986).

(e)K. T. Mak, K. Srinivasachar and N. C. Yang, J. Chem. Soc., Chem. Commun., 1038 (1979).

(f)N. C. Yang and J. Libman, J. Am. Chem. Soc., 94, 1405 (1972).

(g)T. S. Cantrell, J. Org. Chem., 46, 2474 (1981).

(h)K. Kan, Y. Kai, N. Yasuoka and N. Kasai, Bull. Chem. Soc. Jpn., 52, 1634 (1979).

(i)C. Pac, T. Sugioka and H. Sakurai, Chem. Lett., 39 (1972).

102.S. McN. Sieburth and J. Chen, J. Am. Chem. Soc., 113, 8163 (1991).

103.(a) S. McN. Sieburth and P. V. Joshi, J. Org. Chem., 58, 1661 (1993).

(b)S. McN. Sieburth and C. -H. Lin, J. Org. Chem., 59, 3597 (1994).

104.S. McN. Sieburth and K. Ravindran, Tetrahedron Lett., 35, 3861 (1994).

105.F. G. West, C. E. Chase and A. M. Arif, J. Org. Chem., 58, 3794 (1993).

106.Photodimerization of 2-pyrones:

(a)P. de Mayo and R. W. Yip, Proc. Chem. Soc. London, 84 (1964).

(b) P. de Mayo, C. L. McIntosh and R. W. Yip, in Organic Photochemical Synthesis (Ed. R. Srinivasan), Vol. 1, Wiley, New York, 1971. p. 99.

(c)R. Rieke and R. A. Copenhafer, Tetrahedron Lett., 879 (1971).

(d)See also: A. Padwa and R. Hartman, J. Am. Chem. Soc., 86, 4212 (1964).

107.C. E. Chase and J. A. Bender, unpublished results, University of Utah.

324

John M. Nuss and Frederick G. West

108.For additional mechanistic studies of 2-pyrone photochemistry, see:

(a)R. G. S. Pong and J. S. Shirk, J. Am. Chem. Soc., 95, 248 (1973).

(b)B. -S. Huang, R. G. S. Pong, J. Laureni and A. Krantz, J. Am. Chem. Soc., 99, 4154 (1977).

109.For example, see:

(a)T. S. Cantrell, Tetrahedron Lett., 907 (1975).

(b)T. Kobayashi, T. Hirai, J. Tsunetsugo, H. Hayashi and T. Nozoe, Tetrahedron, 31, 1483 (1975) and references cited therein.

For other references concerned with the photochemistry of tropones, see:

(c)T. Mukai, H. Tsurata, A. Takeshita and H. Watanabe, Tetrahedron Lett., 4065 (1968).

(d)T. Tezuka, Y. Akasaki and T. Mukai, Tetrahedron Lett., 1397 (1967).

(e)A. S. Kende and J. E. Lancaster, J. Am. Chem. Soc., 89, 5283 (1967).

(f)T. Tezuka, Y. Akasaki and T. Mukai, Tetrahedron Lett., 5003 (1967).

(g)A. S. Kende, J. Am. Chem. Soc., 88, 5025 (1966).

(h)T. Tezuka, Y. Akasaki and T. Mukai, J. Am. Chem. Soc., 88, 5026 (1966).

110.(a) K. S. Feldman, J. H. Come, A. J. Freyer, B. J. Kosminder and C. M. Smith, J. Am. Chem. Soc., 108, 1327 (1986).

(b)K. S. Feldman, J. H. Come, B. J. Kosminder, C. M. Smith and D. P. Rotella, J. Org. Chem., 54, 592 (1989).

111.K. S. Feldman, M. J. Wu and D. P. Rotella, J. Am. Chem. Soc., 112, 8490 (1990).

112.(a) J. H. Rigby, H. S. Ateeq, N. R. Charles, S. V. Cuisiat, M. D. Ferguson, J. A. Henshilwood, A. C. Krueger, C. O. Ogbu, K. M. Short and M. J. Heeg, J. Am. Chem. Soc., 115, 1382 (1993).

(b)K. Chaffee, P. Huo, J. B. Sheridan, A. Barbieri, A. Aistars, R. A. Lalancette, R. L. Ostrander and A. Rheingold, J. Am. Chem. Soc., 117, 1900 (1995) and references cited therein.

113.(a) S. Oezkar, H. Hurz, D. Neugebauer and C. G. Kreiter, J. Organomet. Chem., 160, 115 (1978).

(b)C. G. Kreiter and H. Kurz, J. Organomet. Chem., 214, 339 (1981).

(c)E. Michels and C. G. Kreiter, J. Organomet. Chem., 252, C1 (1983).

114.J. H. Rigby, Acc. Chem. Res., 26, 579 (1993).

115.J. H. Rigby and H. S. Ateeq, J. Am. Chem. Soc., 112, 6442 (1990).

116.J. H. Rigby and J. A. Henshilwood, J. Am. Chem. Soc., 113, 5122 (1991).

(b)J. H. Rigby, P. Sugathapala and M. J. Heeg, J. Am. Chem. Soc., 117, 8851 (1995).

(c)J. H. Rigby, S. Scribner and M. J. Heeg, Tetrahedron Lett., 36, 8569 (1995).

117.J. H. Rigby and V. P. Sandanayaka, Tetrahedron Lett., 34, 935 (1993).

118.J. H. Rigby, N. M. Niyaz, K. Short and M. J. Heeg, J. Org. Chem., 60, 7720 (1995).

119.J. H. Rigby, H. S. Ateeq and A. C. Kreuger, Tetrahedron Lett., 33, 5873 (1992).

120.J. H. Rigby, G. Ahmed and M. D. Ferguson, Tetrahedron Lett., 34, 5397 (1993).

121.S. C. Stinson, Chem. Eng. News, Oct. 9, 1995, pp. 44 74.

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