First total synthesis of (±)-longianone

Chemical Communications

Volumn , Issue 22, 1999, Pages 2257-2258

  Steel, Patrick G ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

LONGIANONE; MYCOTOXIN; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; FUNGUS; REACTION ANALYSIS; SYNTHESIS;

EID: 0033592790     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907313b     Document Type: Article

References (18)

1. R. L. Edwards, D. J. Maitland, C. L. Oliver, M. S. Pacey, L. Shields and A. J. S. Whalley, J. Chem. Soc., Perkin Trans. 1, 1999, 715.
2. Although structurally similar it appears that the biosyntheses of these natural products are different. Whereas these other natural products are suggested to be produced through the condensation of a triketide with a pentose unit, longianone is derived from 6-methylsalicyclic acid. See R. J. M. Gross, J. Fuscher and D. O'Hagan, Chem. Commun., 1999, 2255.
3. S. L. Midland, N. T. Keen, J. J. Sims, M. M. Midland, M. M. Stayton, V. Burton, M. J. Smith, E. P. Mazzola, K. J. Graham and J. Clardy, J. Org. Chem., 1993, 58, 2940.
4. S. L. Midland, N. T. Keen and J. J. Sims, J. Org. Chem., 1995, 60, 1118.
5. P. Yu, Q. G. Wang, T. Mak and H. Wong, Tetrahedron, 1998, 54, 1783.
6. P. Yu, Y. Yang, Z. Y. Zhang, T. Mak and H. Wong, J. Org. Chem., 1997, 62, 6359.
7. C. Mukai, S. M. Moharram, S. Azukizawa and M. Hanaoka, J. Org. Chem., 1997, 62, 8095.
8. M. Carda, E. Castillo, S. Rodriguez, E. Falomir and J. A. Marco, Tetrahedron Lett., 1998, 39, 8895.
9. H. Yoda, M. Kawauchi, K. Takabe and K. Hosoya, Heterocycles, 1997, 45, 1895 and 1906 and references therein.
10. D. Ichinari, T. Ueki, K. Yoshihara and T. Kinoshita, Chem. Commun., 1997, 1743.
11. Similar radical cyclisations to generate spirocyclic ethers are precedented. See for example, D. S. Middleton, N. S. Simpkins, M. J. Begley and N. K. Terrett, Tetrahedron, 1990, 46, 545.
12. C. J. Hayes and G. Pattenden, Tetrahedron Lett., 1996, 37, 271.
13. H. Hoffmann, B. Schmidt and S. Wolff, Tetrahedron, 1989, 45, 6113.
14. G. Stork and R. Mook, J. Am. Chem. Soc., 1987, 109, 2829.
15. R. J. Linderman and M. Jaber, Tetrahedron Lett., 1994, 35, 5993.
16. The workup of this protiodestannylation is much simplified if the the tin residues are removed by stirring the crude reaction mixture with KF: J. E. Leibner and J. Jacobus, J. Org. Chem., 1979, 44, 449.
17. K. B. Sharpless, R. F. Lauer and A. Y. Teranishi, J. Am. Chem. Soc., 1973, 95, 6137.
18. D. H. R. Barton, D. J. Lester and S. V. Ley, J. Chem. Soc., Perkin Trans. 1, 1980, 2209.