Total synthesis of (±)-2-pupukeanone

Journal of Organic Chemistry

Volumn 61, Issue 15, 1996, Pages 4967-4970

  Chang, Nein Chen ^a   Chang, Chi Kang ^a  

^a NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PUPUKEANONE; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030055643     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9603338     Document Type: Article

References (19)

1. Burreson, B. J.; Scheuer, P. J.; Finer, J.; Clardy, J. J. Am. Chem. Soc. 1975, 97, 4763.
2. (a) Corey, E. J.; Behforouz, M.; Ishiguro, M. J. Am. Chem. Soc. 1979, 101, 1608.
3. (b) Yamamoto, H.; Sham, H. L. J. Am. Chem. Soc. 1979, 101, 1609.
4. Corey, E. J.; Ishiguro, M. Tetrahedron. Lett. 1979, 2745.
5. (a) Schiehser, G. A.; White, J. D. J. Org. Chem. 1980, 45, 1864.
6. (b) Hsieh, S. L.; Chiu, C. T.; Chang, N. C. J. Org. Chem. 1989, 54, 3820.
7. Frater, G.; Wenger, J. Helv. Chim. Acta 1984, 64, 1702.
8. (a) Brown, E. D.; Clarkson, R.; Leeney, T. J.; Robinson, G. E. J. Chem. Soc., Perkin Trans. 1, 1978, 1507.
9. (b) Chang, N. C.; Lu, W. F.; Tseng, C. Y. J. Chem. Soc., Chem. Commun. 1988, 182.
10. (c) Chang, N. C.; Chiu, C. T. J. Chin. Chem. Soc. 1993, 40, 379.
11. Ibuka, T.; Hayashi, K.; Minakata, H.; Ito, Y.; Inubushi, Y. Can. J. Chem. 1979, 57, 1579.
12. Hsu, L. F.; Chang, C. P.; Chang, N. C. J. Org. Chem. 1993, 58, 4756.
13. Sell, C. S. Aust. J. Chem. 1975, 28, 1383.
14. Paquette, L. A.; DeRussy, D. T.; Pegg, N. A.; Taylor, R. T.; Zydowsky, T. M. J. Org. Chem. 1989, 54, 4576.
15. Schwartz, A.; Madan, P. J. Org. Chem. 1986, 51, 5463.
16. (a) Miyashita, M.; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772.
17. (b) Rosen, T.; Taschner, M. J.; Thomas, J. A.; Heathcock, C. H. J. Org. Chem. 1985, 50, 1190.
18. Hydrogenation process furnished only one product 4 as judged by NMR spectra.
19. We thank professor G. Frater for providing us the NMR, IR, and mass spectra for comparison.