Two carbon ring expansion by photochemical ring opening of electrophilic cyclobutenes

Tetrahedron Letters

Volumn 38, Issue 43, 1997, Pages 7551-7554

  Miesch, Michel ^a   Mislin, Gaëtan ^b   Franck Neumann, Michel ^b  

^a CNRS   (France)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

AZULENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOLYSIS; REACTION ANALYSIS;

EID: 0030861284     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10032-6     Document Type: Article

References (25)

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3. The Total Synthesis of Natural Products Vol. V. J.ApSimon, John Wiley and Sons 1983, p 333-384; Zhuzbaev, B.T.; Adekenov, S.M.; Veselovskii, V.V. Russ. Chem. Rev. 1995, 64, 187-200; Vandewalle, M.; De Clerq, P. Tetrahedron 1985, 41, 1767-1831; Ghisalberti, E.L. Phytochemistry 1994, 37, 597-623.
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5. See for example: Hikino, H.; De Mayo, P. J. Amer. Chem. Soc. 1964, 86, 3582-3583; Liu, H.J.; Lee S.P. Tetrahedron Lett. 1977, 3699-3702; Sampath, V.; Lund, E.C.; Knudsen, M.J.; Olmstead, M.M.; Schore, N.E. J. Org. Chem. 1987, 52, 3595-3603; Pak, C.S.; Kim, S.K.; Lee, H.K. Tetrahedron Lett. 1991, 32, 6011-6014; Lange, G.L.; Gottardo, C. Tetrahedron Lett. 1994, 35 6607-6610; ibid. 1994, 35, 8513-8513.
6. See for example: Hikino, H.; De Mayo, P. J. Amer. Chem. Soc. 1964, 86, 3582-3583; Liu, H.J.; Lee S.P. Tetrahedron Lett. 1977, 3699-3702; Sampath, V.; Lund, E.C.; Knudsen, M.J.; Olmstead, M.M.; Schore, N.E. J. Org. Chem. 1987, 52, 3595-3603; Pak, C.S.; Kim, S.K.; Lee, H.K. Tetrahedron Lett. 1991, 32, 6011-6014; Lange, G.L.; Gottardo, C. Tetrahedron Lett. 1994, 35 6607-6610; ibid. 1994, 35, 8513-8513.
7. See for example: Hikino, H.; De Mayo, P. J. Amer. Chem. Soc. 1964, 86, 3582-3583; Liu, H.J.; Lee S.P. Tetrahedron Lett. 1977, 3699-3702; Sampath, V.; Lund, E.C.; Knudsen, M.J.; Olmstead, M.M.; Schore, N.E. J. Org. Chem. 1987, 52, 3595-3603; Pak, C.S.; Kim, S.K.; Lee, H.K. Tetrahedron Lett. 1991, 32, 6011-6014; Lange, G.L.; Gottardo, C. Tetrahedron Lett. 1994, 35 6607-6610; ibid. 1994, 35, 8513-8513.
8. See for example: Hikino, H.; De Mayo, P. J. Amer. Chem. Soc. 1964, 86, 3582-3583; Liu, H.J.; Lee S.P. Tetrahedron Lett. 1977, 3699-3702; Sampath, V.; Lund, E.C.; Knudsen, M.J.; Olmstead, M.M.; Schore, N.E. J. Org. Chem. 1987, 52, 3595-3603; Pak, C.S.; Kim, S.K.; Lee, H.K. Tetrahedron Lett. 1991, 32, 6011-6014; Lange, G.L.; Gottardo, C. Tetrahedron Lett. 1994, 35 6607-6610; ibid. 1994, 35, 8513-8513.
9. See for example: Hikino, H.; De Mayo, P. J. Amer. Chem. Soc. 1964, 86, 3582-3583; Liu, H.J.; Lee S.P. Tetrahedron Lett. 1977, 3699-3702; Sampath, V.; Lund, E.C.; Knudsen, M.J.; Olmstead, M.M.; Schore, N.E. J. Org. Chem. 1987, 52, 3595-3603; Pak, C.S.; Kim, S.K.; Lee, H.K. Tetrahedron Lett. 1991, 32, 6011-6014; Lange, G.L.; Gottardo, C. Tetrahedron Lett. 1994, 35 6607-6610; ibid. 1994, 35, 8513-8513.
10. See for example: Hikino, H.; De Mayo, P. J. Amer. Chem. Soc. 1964, 86, 3582-3583; Liu, H.J.; Lee S.P. Tetrahedron Lett. 1977, 3699-3702; Sampath, V.; Lund, E.C.; Knudsen, M.J.; Olmstead, M.M.; Schore, N.E. J. Org. Chem. 1987, 52, 3595-3603; Pak, C.S.; Kim, S.K.; Lee, H.K. Tetrahedron Lett. 1991, 32, 6011-6014; Lange, G.L.; Gottardo, C. Tetrahedron Lett. 1994, 35 6607-6610; ibid. 1994, 35, 8513-8513.
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21. We also used the corresponding pyrrolidino (instead of morpholino) cyclobutenic esters but these compounds are unstable and their thermal treatment leads only to a complex mixture of products.
22. Clark R.D., Untch K.G. J. Org. Chem. 44:1979;248-253.
23. Woodward, R.B.; Hoffmann, R. The Conservation of Orbital Symmetry, Verlag Chemie Weinhein 1971.
24. Doyle has shown that the [2+2] cycloaddition of 1-methoxyindene with ACDM gives the corresponding cycloadduct with opens up either thermally (78 % yield) or photochemically (pyrex photoreactor; quant.). To our knowledge, this is the sole other report concerning the photochemical ring expansion of such type electrophilic cyclobutenes. Doyle, T.W. Can. J. Chem. 1970, 48, 1629-1632.
25. 2 and then treated in acidic conditions (HCl 10%, THF, 20°C). The cis ring junction of compound 16 was secured by COSY and NOESY spectra.