Synthesis of Highly Substituted Bicyclo[3.2.0]heptanones from 3-Homoallylcyclobutenones. A Total Synthesis of (±)-Precapnelladiene

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3792-3793

  MacDougall, James M ^a   Turnbull, Philip ^a,b   Verma, Sharad K ^a   Moore, Harold W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001517186     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970644y     Document Type: Article

References (24)

1. Moore, H. W.; Xia, H.; Xu, S. L. J. Org. Chem. 1991, 56, 6094.
2. Moore, H. W.; Xu, S. L. J. Org. Chem. 1989, 54, 6018.
3. Santora, V. J.; Moore, H. W. J. Org. Chem. 1996, 61, 7976.
4. Santora, V. J.; Moore, H. W. J. Am. Chem. Soc. 1995, 117, 8486.
5. For previous syntheses of precapnelladiene see: (a) Birch, A. M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1913. (b) Mehta, G.; Murthy, A. N. J. Org. Chem. 1987, 52, 2875. (c) Kinney, W. A.; Coghlan, M. J.; Paquette, L. A. J. Am. Chem. Soc. 1985, 107, 7352. (d) Petasis, N. A.; Patane, M. A. Tetrahedron Lett. 1990, 31, 6799.
6. For previous syntheses of precapnelladiene see: (a) Birch, A. M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1913. (b) Mehta, G.; Murthy, A. N. J. Org. Chem. 1987, 52, 2875. (c) Kinney, W. A.; Coghlan, M. J.; Paquette, L. A. J. Am. Chem. Soc. 1985, 107, 7352. (d) Petasis, N. A.; Patane, M. A. Tetrahedron Lett. 1990, 31, 6799.
7. For previous syntheses of precapnelladiene see: (a) Birch, A. M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1913. (b) Mehta, G.; Murthy, A. N. J. Org. Chem. 1987, 52, 2875. (c) Kinney, W. A.; Coghlan, M. J.; Paquette, L. A. J. Am. Chem. Soc. 1985, 107, 7352. (d) Petasis, N. A.; Patane, M. A. Tetrahedron Lett. 1990, 31, 6799.
8. For previous syntheses of precapnelladiene see: (a) Birch, A. M.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1983, 1913. (b) Mehta, G.; Murthy, A. N. J. Org. Chem. 1987, 52, 2875. (c) Kinney, W. A.; Coghlan, M. J.; Paquette, L. A. J. Am. Chem. Soc. 1985, 107, 7352. (d) Petasis, N. A.; Patane, M. A. Tetrahedron Lett. 1990, 31, 6799.
9. Gayo, L. Ph.D. Dissertation, University of California at Irvine, 1992.
10. Also see: Edwards, J. P.; Krysan, D. J.; Liebeskind, L. S. J. Org, Chem. 1993, 58, 3942.
11. Turnbull, P.; Heilemen, M. J.; Moore H. W. J. Org. Chem. 1996, 61, 2584.
12. Also see: Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Permagon Press: Oxford, 1992; Chapter 3.
13. The structures of 7a-e as well as the other new compounds (9a-e, 10d,e, 11-14) reported here are based upon their spectral data including NOE studies, which are in agreement with their assigned stereochemistry.
14. For examples of intramolecular ketene/alkene cycloadditions leading to bicyclo[3.1.1] systems see: Allentoff, A. J.; Kulkarni, Y. S.; Snyder, B. B. J. Org. Chem. 1988, 53, 5320.
15. (a) Houk, K. N.; Rondan, N. G. J. Am. Chem. Soc. 1985, 107, 2099.
16. (b) Niwayama, S.; Kallel, E. A.; Sheu, C.; Houk, K. N. J. Org. Chem. 1996, 61, 2517.
17. 1H NMR analysis.
18. Isolated as a 4:1 mixture of diastereomers.
19. The structure of the major aldehyde is based upon its spectral properties as well as a complete X-ray analysis.
20. W-2 Raney nickel was prepared by the method of Monzigo. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, pp 181-183.
21. For a general review of the oxy-Cope reaction see: Paquette, L. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 609.
22. For oxy-Cope rearrangements on similar bicyclo[3.2.0] ring systems, see: Gadwood, R. C.; Lett, R. M.; Wissinger, J. E. J. Am. Chem. Soc. 1986, 108, 6343 and references cited therein.
23. Takai, K.; Sato, M.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1984, 57, 108.
24. 1H NMR spectrum of an authentic sample of (±)-precapnelladiene.