Cyclobutenone-based syntheses of polyquinanes and bicyclo[6.3.0]undecanes by tandem anionic oxy-cope reactions. Total synthesis of (±)-precapnelladiene

Journal of Organic Chemistry

Volumn 63, Issue 20, 1998, Pages 6905-6913

  MacDougall, James M ^a   Santora, Vincent J ^a   Verma, Sharad K ^a   Turnbull, Philip ^a   Hernandez, Cameron R ^a   Moore, Harold W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000256044     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980712w     Document Type: Article

References (37)

1. Present address: Amgen Corp., Thousand Oaks, CA 91320-1789.
2. Present address: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037.
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7. For examples see the following and references cited therein: Santora, V. S.; Moore, H. W. J. Org. Chem. 1996, 61, 7976.
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11. For a preliminary account of this work see: Santora, V. S.; Moore, H. W. J. Am. Chem. Soc. 1995, 777, 8486.
12. For recent examples of other tandem reactions involving oxyCope reactions, see: Jacobi, P. A.; Armacost, L. M.; Brielmann, H. L.; Cann, R. O.; Kravitz, J. I.; Martinelli, M. J. J. Org. Chem. 1994, 59, 5292-5304.
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17. The presence of the bicyclo[3.2.0]heptenol could not be detected by analysis of the crude reaction mixture that was obtained upon quenching the oxy-Cope reaction at -78 °C.
18. For reviews of the oxy-Cope rearrangement, see: (a) Paquette, L. A. Angew. Chem., Int. Ed. Engl. 1990,29, 609-626.
19. (b) Lutz, R. P. Chem. Rev. 1984, 84, 206-290.
20. For an elegant example of this rearrangement on similar bicyclo[3.2.0] systems, see: Gadwood, R. C.; Lett, R. M.; Wissinger, J. E. J. Am. Chem. Soc. 1986, 108, 6343.
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22. For the preparation of dialkyl squarates from squarie acid, see: Lui, H.; Tamooka, C. S.; Moore, H. W. Synth. Commun. 1997, 27, 2177.
23. This is an excellent procedure for the regiospecific preparation of substituted cyclobutenones. For more details see: Gayo, L.; Winters, M. P.; Moore, H. W. J. Org. Chem. 1992, 57, 6896.
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30. For an excellent review on the synthesis of eight-membwed rings see: Petasis, N. S.; Patane, M. A. Tetrahedron 1992, 5757.
31. For selected other methods of constructing the bicyclo[6.3.0]-undeeane ring system, see: (a) Wender, P. A.; Nuss, J. M.; Smith, D. B.; SuarezSobrino, A. J. Org. Chem. 1997, 62, 2, 4908.
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34. For a preliminary account of the precapnelladiene synthesis see: MacDougall, J. M.; Turnbull, P.; Verma, S. K.; Moore, H. W. J. Org. Chem. 1997, 62, 3792.
35. 1H NMR spectrum of an authentic sample of (±)-precapnelladiene.
36. The C-3 methyl on the a-face is deshielded relative to the C-3 methyl group on the β-face, which is above the plane of the C-3b/C-4 carbon double bond (Scheme 6). See, for example: Romo De Vivar, A.; Nieto, D. A.; Gavino, R.; Ana-Lidia Ferez, C. Phytochemistry 1995, 40, 167.
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