Total synthesis of racemic lasidiol via intramolecular [4+3] cycloaddition

Tetrahedron Letters

Volumn 41, Issue 9, 2000, Pages 1375-1379

  Kreiselmeier, Günter ^a   Föhlisch, Baldur ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

LASIDIOL; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HYDROGENATION; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0343049068     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02296-0     Document Type: Article

References (34)

1. (a) For a review, see: Gonzáles, A. G.; Barrera, J. B. In Progress in the Chemistry of Organic Natural Products; Herz, W.; Kirby, G. W.; Moore, R. E.; Steglich, W.; Tamm, Ch., Eds.; Springer Verlag: Wien, 1995; Vol. 64, p. 1.
2. (b) Casinovi, C. G.; Cerrini, S.; Motl, O.; Fardella, G.; Fedeli, W.; Gavuzzo, E.; Lamba, D. Collect. Czech. Chem. Commun. 1983, 48, 2411.
3. (a) Yamasaki, M. J. Chem. Soc., Chem. Commun. 1972, 606.
4. (b) Naegeli P.; Kaiser R. Tetrahedron Lett. 1972 20 2013
5. (c) Audenaert, F.; De Keukeleire, D.; Vandewalle, M. Tetrahedron 1987, 43, 5593.
6. (d) De Broissia, H.; Levisalles, J.; Rudler, H. J. Chem. Soc., Chem. Commun. 1972, 855.
7. (e) Harayama, T.; Shinkai, Y.; Hashimoto, Y.; Fukushi, H.; Inubushi, Y. Tetrahedron Lett. 1983, 24, 5241.
8. Wiemer, D. F.; Ales, D. C. J. Org. Chem. 1981, 46, 5449.
9. (a) Föhlisch B.; Herter R. Chem. Ber
10. (b) Kaiser, R.; Föhlisch, B. Helv. Chim. Acta 1990, 73, 1504.
11. (c) Harmata, M. Tetrahedron 1997, 53, 6235.
12. (a) Föhlisch, B.; Kreiselmeier, G., submitted for publication.
13. (b) Kreiselmeier, G. Dissertation, Universität Stuttgart, 1998.
14. For a review on ring-opening reactions of oxabicyclic compounds, see: Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 1.
15. Harmata, M.; Carter, K. W. Tetrahedron Lett. 1997, 38, 7985.
16. Scholz, S.; Marschall-Weyerstahl, H.; Weyerstahl, P. Liebigs Ann. Chem. 1985, 1935.
17. Cernayová, M.; Kovác, J.; Dandárová, M.; Hasová, B.; Palovcík, R. Collect. Czech. Chem. Commun. 1976, 41, 764.
18. Johnson, R. L. J. Med. Chem. 1984, 27, 1351.
19. Petragnani, N.; Yonashiro M. Synthesis 1982, 521.
20. Krapcho, A. P.; Weimaster, J. F.; Eldridge, J. M.; Jahngen Jr., E. G. E.; Lovey, A. J.; Stephens, W. P. J. Org. Chem. 1978, 43, 138.
21. Barluenga, J.; Llavona, L.; Concellón, J. M.; Yus, M. J. Chem. Soc., Perkin Trans 1 1991, 297.
22. (a) Föhlisch, B.; Gehrlach, E.; Herter, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 137.
23. (b) Angew. Chem. Suppl. 1982, 241.
24. (a) Kende A.S. Org. React. 1960 11 261
25. (b) For Favorskii rearrangement in TFE, see: Föhlisch, B.; Gehrlach, E.; Henle, G. J. Chem. Res. (S) 1991, 136.
26. (c) J. Chem. Res. (M) 1991, 1462, and Ref. 5b.
27. Hoffmann, H. M. R.; Clemens, K. E.; Smithers, R. H. J. Am. Chem. Soc. 1972, 94, 3940.
28. Takaya, H.; Makino, S.; Hayakawa, Y.; Noyori, R. J. Am. Chem. Soc. 1978, 100, 1765.
29. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-137334. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax int. code +44(1223)336-033; E-mail: deposit@ccdc.cam.ac.uk].
30. According to Chemical Abstracts, Index Guide, Appendix IV, ¶ 203, I (D), the descriptors α and β are used. The α-side is defined by the oxygen-bridge.
31. Platzer, N.; Goasdoue, N.; Davoust, D. Magn. Reson. Chem. 1987, 25, 311.
32. Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1.
33. Cramer, C. J.; Barrows, S. E. J. Org. Chem. 1998, 63, 5523.
34. Treu, J.; Hoffmann, H. M. R. J. Org. Chem. 1997, 62, 4650.