Intramolecular 4+3 cycloadditions. A total synthesis of aphanamol

Tetrahedron Letters

Volumn 38, Issue 46, 1997, Pages 7985-7988

  Harmata, Michael ^a   Carter, Kevin W ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

APHANAMOL; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0030771033     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10146-0     Document Type: Article

References (29)

1. For reviews of 4+3 cycloadditions, see: (a) Hosomi, A. and Tominaga, Y. (1991) [4+3] cycloadditions. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I. Eds.; Pergamon: Oxford, Vol. 5, Chapter 5.1, pp 593-615.
2. (b) Hoffmann, H.M.R. Angew. Chem. Intl. Ed. Engl. 1984. 23, 1.
3. (c) Mann, J. Tetrahedron 1986, 42, 4611.
4. (d) Noyori, R. and Hayakawa, Y. Org. React. 1983, 29, 163-344.
5. For a review of intramolecular 4+3 cycloadditions, see: (a) Harmata, M. Tetrahedron 1997, 53, 6235.
6. (b) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1997, Vol. 4, pp 41-86.
7. Hoffmann H.M.R., Henning R. Helv. Chim. Acta. 66:1983;828.
8. Nishizawa M., Inoue A., Hayashi Y., Sastrapradja S., Kosela S., Iwashita T. J. Org. Chem. 49:1984;3660.
9. Yoshida, T.; Muraki, S.; Takahashi, K.; Katao, T.; Kabuto, C.; Suzuki, T.; Uyehara, T.; Ohnuma, T. J. Chem. Soc. Chem. Commun. 1979, 512.
10. Mehta G., Krishnamurthy N., Karra S.R. J. Am. Chem. Soc. 113:1991;5765.
11. Hansson T., Wickberg B. J. Org. Chem. 57:1992;5370.
12. Shizuri Y., Yamaguchi S., Terada Y., Yamamura S. Tetrahedron Lett. 27:1986;57.
13. (a) Hoffmann, H.M.R.; Matthei, J. Chem. Ber. 1980, 113, 3837.
14. (b) Hoffmann, H.M.R.; Eggert, U.; Gibbels, U.; Giesel, K.; Koch, O.; Lies, R.; Rabe, J. Tetrahedron 1988, 44, 3899.
15. Harmata M., Jones D.E. Tetrahedron Lett. 37:1996;783.
16. (a) Harmata, M.; Jones, D.E. J. Org. Chem. 1997, 62, 1578.
17. (b) Kende, A.S.; Huang, H. Tetrahedron Lett. 1997, 38, 3353.
18. (a) Light, K.K.; Ogden, N.; Schreiber, W.L.; McGhie, J.A.; Schreck, R.P.; Yoshida, T.; Schreiber, L.B.; Muralidhara, R. US Patent 4 412 083, 1983; Chem Abstr. 1984, 100:P85960u.
19. (b) Stork, G.; Bizzolara, A.; Landesman, H.; Szmuskovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207.
20. (a) Harmata, M.; Carter, K. Synth. Commun. 1997, 27, 3027.
21. (b) Ukai, J.; Ikeda, Y.; Ikeda, N.; Yamamoto, H. Tetrahedron Lett. 1983, 24, 4029.
22. Grell W.V., Machleidt H. Liebigs. Ann. Chem. 699:1966;53.
23. The ester precursor of the alcohol was also obtained as an inseparable mixture.
24. (a) Giguere, R.J.; Tassely, S.M.; Rose, M.I.; Krishnamurthy, V.V. Tetrahedron Lett. 1990, 31, 4577.
25. (b) Giguere, R.J.; Duncan, S.M.; Bean, J.M.; Purvis, L. Tetrahedron Lett. 1988, 29, 6071.
26. 2O; Yield: 18%.
27. Harmata M., Gamlath C.B., Barnes C.L., Jones D.E. J. Am. Chem. Soc. 60:1995;5077.
28. 1H NMR and capillary GC. The determination of structural and stereochemical assignments is in progress and will be reported elsewhere.
29. 13C NMR and IR spectral data as well as satisfactory combustion analysis or high resolution exact mass data.