Participation of aromatic groups in oxy-cope reaction sequences. Synthesis of highly substituted polyquinane ring systems

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 7976-7977

  Santora, Vincent J ^a   Moore, Harold W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029827950     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9613693     Document Type: Article

References (14)

1. For recent reviews and leading references, see: (a) Paquette, L. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 609-626. (b) Paquette, L. A. Synlett 1990, 67-73. (c) Lutz, R. P. Chem. Rev. 1984, 206-243. (d) Wilson, S. R. Org. React. 1993, 43, 95-246.
2. For recent reviews and leading references, see: (a) Paquette, L. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 609-626. (b) Paquette, L. A. Synlett 1990, 67-73. (c) Lutz, R. P. Chem. Rev. 1984, 206-243. (d) Wilson, S. R. Org. React. 1993, 43, 95-246.
3. For recent reviews and leading references, see: (a) Paquette, L. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 609-626. (b) Paquette, L. A. Synlett 1990, 67-73. (c) Lutz, R. P. Chem. Rev. 1984, 206-243. (d) Wilson, S. R. Org. React. 1993, 43, 95-246.
4. For recent reviews and leading references, see: (a) Paquette, L. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 609-626. (b) Paquette, L. A. Synlett 1990, 67-73. (c) Lutz, R. P. Chem. Rev. 1984, 206-243. (d) Wilson, S. R. Org. React. 1993, 43, 95-246.
5. (a) Jung, M. E.; Hudspeth, J. P. J Am. Chem. Soc. 1980, 102, 2463-2464.
6. (b) Jung, M. E.; Hudspeth, J. P. J. Am. Chem. Soc. 1978, 100, 4309-4311.
7. (c) Marvell, E. N.; Almond, S. W. Tetrahedron Lett. 1979, 21, 2779-2780.
8. For previous work in this area, see: (a) Santora, V. J.; Moore, H. W. J. Am. Chem. Soc. 1995, 117, 8486-8487. (b) Xu, S. L.; Xia, H.; Moore, H. W. J. Org. Chem. 1991, 56, 6094-6103. (c) Xu, S. L.; Moore, H. W. J. Org. Chem. 1989, 54, 6018-6021.
9. For previous work in this area, see: (a) Santora, V. J.; Moore, H. W. J. Am. Chem. Soc. 1995, 117, 8486-8487. (b) Xu, S. L.; Xia, H.; Moore, H. W. J. Org. Chem. 1991, 56, 6094-6103. (c) Xu, S. L.; Moore, H. W. J. Org. Chem. 1989, 54, 6018-6021.
10. For previous work in this area, see: (a) Santora, V. J.; Moore, H. W. J. Am. Chem. Soc. 1995, 117, 8486-8487. (b) Xu, S. L.; Xia, H.; Moore, H. W. J. Org. Chem. 1991, 56, 6094-6103. (c) Xu, S. L.; Moore, H. W. J. Org. Chem. 1989, 54, 6018-6021.
11. Lithium and cerium reagents were prepared using standard methods. For leading references, see: (a) Wakefield, B. J. Organolithium Methods; Academic Press: New York, 1988. (b) Brandsma, L.; Verkruijsse, H. Preparative Polar Organometallic Chemistry 1; Springer-Verlag: Berlin, 1987.
12. Lithium and cerium reagents were prepared using standard methods. For leading references, see: (a) Wakefield, B. J. Organolithium Methods; Academic Press: New York, 1988. (b) Brandsma, L.; Verkruijsse, H. Preparative Polar Organometallic Chemistry 1; Springer-Verlag: Berlin, 1987.
13. 13C NMR, IR, and high-resolution mass spectral data have been obtained for all new compounds except for 9a,b, which was observed to be quite unstable to purification techniques. Thus, its spectral data were obtained on the partially purified samples.
14. Phenyllithium also reacts with 1 to give only a 10% yield of a polyquinane analogous in structure to 11. The major product (60%) is a bicyclo[2.2.1]heptene resulting from a 1.3-sigmatropic shift at the alkoxide stage. An analogous 1,3-shift takes place when 1 was treated with 2-lithio-1-methylpyrrole.