The synthesis of angularly fused tricyclic compounds via tandem ring closing metathesis reactions

Chemical Communications

Volumn , Issue 12, 2000, Pages 1035-1036

  Bassindale, Martin J ^a   Edwards, Andrew S ^a   Hamley, Peter ^b   Adams, Harry ^a   Harrity, Joseph P A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

TRICYCLIC AROMATIC COMPOUND;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLIZATION; MOLECULAR MODEL; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034697870     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b002136i     Document Type: Article

References (20)

1. For representative alkaloid examples, see: K. M. Werner, J. M. de los Santos and S. M. Weinreb, J. Org. Chem., 1999, 64, 686; W. H. Pearson and Y. Ren, J. Org. Chem., 1999, 64, 688; C. Sha, F. Lee and C. Chang, J. Am. Chem. Soc., 1999, 121, 9875; for synthetic approaches to triquinanes, see: G. Mehta and S. Srikrishna, Chem. Rev., 1997, 97, 671.
2. For representative alkaloid examples, see: K. M. Werner, J. M. de los Santos and S. M. Weinreb, J. Org. Chem., 1999, 64, 686; W. H. Pearson and Y. Ren, J. Org. Chem., 1999, 64, 688; C. Sha, F. Lee and C. Chang, J. Am. Chem. Soc., 1999, 121, 9875; for synthetic approaches to triquinanes, see: G. Mehta and S. Srikrishna, Chem. Rev., 1997, 97, 671.
3. For representative alkaloid examples, see: K. M. Werner, J. M. de los Santos and S. M. Weinreb, J. Org. Chem., 1999, 64, 686; W. H. Pearson and Y. Ren, J. Org. Chem., 1999, 64, 688; C. Sha, F. Lee and C. Chang, J. Am. Chem. Soc., 1999, 121, 9875; for synthetic approaches to triquinanes, see: G. Mehta and S. Srikrishna, Chem. Rev., 1997, 97, 671.
4. For representative alkaloid examples, see: K. M. Werner, J. M. de los Santos and S. M. Weinreb, J. Org. Chem., 1999, 64, 686; W. H. Pearson and Y. Ren, J. Org. Chem., 1999, 64, 688; C. Sha, F. Lee and C. Chang, J. Am. Chem. Soc., 1999, 121, 9875; for synthetic approaches to triquinanes, see: G. Mehta and S. Srikrishna, Chem. Rev., 1997, 97, 671.
5. For recent reviews on the ring closing metathesis reaction in organic synthesis see: S. K. Armstrong, J. Chem. Soc., Perkin Trans., 1, 1998, 371; R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413; M. Schuster and S. Blechert, Angew. Chem., Int. Ed. Engl., 1997, 36, 2036.
6. For recent reviews on the ring closing metathesis reaction in organic synthesis see: S. K. Armstrong, J. Chem. Soc., Perkin Trans., 1, 1998, 371; R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413; M. Schuster and S. Blechert, Angew. Chem., Int. Ed. Engl., 1997, 36, 2036.
7. For recent reviews on the ring closing metathesis reaction in organic synthesis see: S. K. Armstrong, J. Chem. Soc., Perkin Trans., 1, 1998, 371; R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413; M. Schuster and S. Blechert, Angew. Chem., Int. Ed. Engl., 1997, 36, 2036.
8. M. J. Bassindale, P. Hamley, A. Leitner and J. P. A. Harrity, Tetrahedron Lett., 1999, 40, 3247.
9. For other examples of tandem diene metathesis reactions, see: (a) W. J. Zuercher, M. Hashimoto and R. H. Grubbs, J. Am. Chem. Soc., 1996, 118, 6634;
10. (b) S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626;
11. (c) W. J. Zuercher, M. Scholl and R. H. Grubbs, J. Org. Chem., 1998, 63, 4291;
12. (d) M. Lautens and G. Hughes, Angew. Chem., Int. Ed., 1999, 38, 129;
13. (e) C. Baylon, M. Heck and C. Mioskowski, J. Org. Chem., 1999, 64, 3354;
14. (f) A. H. Hoveyda, in Topics in Organometallic Chemistry, ed. A. Furstner, Springer-Verlag, Berlin, 1998, vol. 1, pp. 105-132.
15. We have isolated and tentatively assigned (NMR and mass spectrometry) compounds II and III from the reaction mixture. Their rigorous characterisation is currently underway and will form part of a full account. (formula presented)
16. -1 using AM1 semiempirical methods implemented using Spartan™ software. The assignment of 4 was based on X-ray crystallographic analysis.
17. In the course of this study the RCM reaction of diene 6 was reported to proceed in good yield (77%) at room temperature: S. Kotha, E. Manivannan, T. Ganesh, N. Sreenivasachary and A. Deb, Synlett, 1999, 1618. This result could not be reproduced in our hands.
18. Prepared by addition of diol 12 to oxalyl chloride in the presence of pyridine and DMAP catalyst.
19. Additionally, the poor reactivity of the cyclohexane system may originate from the inability of the appropriate alkene units to attain sufficient alignment for metathesis. We thank a referee for this suggestion.
20. All compounds exhibited satisfactory analytical and spectral data.