The total synthesis of favelanone

Tetrahedron Letters

Volumn 37, Issue 37, 1996, Pages 6797-6798

  Ng, Wendy ^a   Wege, Dieter ^a  

^a UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; FAVELANONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030576916     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)01482-7     Document Type: Article

References (13)

1. 1. Endo, Y., Ohta, T., and Nozoe, S., Tetrahedron Lett., 1991, 32, 5555.
2. 2. The absolute stereochemistry of (+)-favelanone is not known; enantiomer (1) is depicted arbitrarily.
3. 3. Endo, Y., Ohta, T., and Nozoe, S., Tetrahedron Lett., 1991, 32, 3083.
4. 4. Ghosh, A. K., Ray, C., and Ghatak, U. R., Tetrahedron Lett., 1992, 33, 655; Ghosh, A. K., Mukhopadhyay (née Ray), C., and Ghatak, U. R., J. Chem. Soc. Perkin Trans 1, 1994, 327. For a different approach see Ho, T.-L., and Chen, C.-K., Tetrahedron, 1995, 51, 5819.
5. 4. Ghosh, A. K., Ray, C., and Ghatak, U. R., Tetrahedron Lett., 1992, 33, 655; Ghosh, A. K., Mukhopadhyay (née Ray), C., and Ghatak, U. R., J. Chem. Soc. Perkin Trans 1, 1994, 327. For a different approach see Ho, T.-L., and Chen, C.-K., Tetrahedron, 1995, 51, 5819.
6. 4. Ghosh, A. K., Ray, C., and Ghatak, U. R., Tetrahedron Lett., 1992, 33, 655; Ghosh, A. K., Mukhopadhyay (née Ray), C., and Ghatak, U. R., J. Chem. Soc. Perkin Trans 1, 1994, 327. For a different approach see Ho, T.-L., and Chen, C.-K., Tetrahedron, 1995, 51, 5819.
7. 5. Ramirez, F., and Kirby, A. F., J. Am. Chem. Soc., 1952, 74, 4331.
8. 6 Billups, W. E., Haley, M. M., and Lee, G.-A., Chem. Rev., 1989, 89, 1147.
9. 7. Kametani, T., Takahashi, K., Ihara, M., and Fukomoto, K., J. Chem. Soc. Perkin Trans. 1, 1976, 389.
10. 8. The addition is highly regioselective; signals ascribable to the isomeric product were not observed in the spectrum of the crude reaction product.
11. 9. Bromo dione (12) was accompanied by favelanone (1) (ca. 15%) suggesting that metal-halogen exchange occurs in (4) and/or (2) during the reaction.
12. 10. We thank Professor Tomihisa Ohta for providing spectral data of natural favelanone.
13. 11. For a previous example see Evans, J. C., Klix, R. C., and Bach, R. D., J. Org. Chem., 1988, 53, 5519.