Formal asymmetric synthesis of pentalenolactone E and pentalenolactone F 2. Construction of the angular diquinanoid δ-lactone

European Journal of Organic Chemistry

Volumn , Issue 2, 1998, Pages 275-289

  Herrmann, Eva ^a   Gais, Hans Joachim ^a   Rosenstock, Bernd ^a   Raabe, Gerhard ^a   Lindner, Hans Jörg ^b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Asymmetric synthesis; Kauffmann methylenation; Natural products; Pentalenolactones E and F; Selenide elimination

Indexed keywords

EID: 0002747007     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199802)1998:2<275::AID-EJOC275>3.0.CO;2-Z     Document Type: Article

References (41)

1. B. Rosenstock, H.-J. Gais, E. Herrmann, G. Raabe, P. Binger, A. Freund, P. Wedemann, C. Krüger, H. J. Lindner, Eur. J. Org. Chem. 1998, 257-273, proceeding paper.
2. In this paper the terms diquinane and triquinane are also used for the designation of compounds containing five-membered heterocyclic rings.
3. [3a] J pappas, W, Klaveney, E. Gaucher, M. Berger, Tetrahedron Lett. 1966, 4237-4278.
4. [3b] M. Trachsel, R. Keese, Helv. Chim. Acta 1988, 71, 363-368.
5. M. Schlosser, B. Schaub, Chimia 1982, 36, 396-397.
6. E. Herrman, Ph. D. Thesis, RWTH Aachen, 1995.
7. B. Rosenstock, Ph. D. Thesis, TH Darmstadt, 1990.
8. L. Lombarde, Org. Synth. 1987, 65, 81-89.
9. C. R. Johnson, B. D. Tait, J. Org. Chem. 1987, 52, 281-283.
10. T. Imamoto, N. Takiyama, K. Nakamura, T. Hatajima, Y. Kamiya, J. Am. Chem. Sac. 1989, 111, 4392-4398.
11. [10a] T Kauffmann, R. Abeln, S. Welke, D. Wingbermühle, Angew. Chem. 1986, 98, 927-928; Angew. Chem. Int. Ed Engl. 1986, 25, 910-911.
12. [10a] T Kauffmann, R. Abeln, S. Welke, D. Wingbermühle, Angew. Chem. 1986, 98, 927-928; Angew. Chem. Int. Ed Engl. 1986, 25, 910-911.
13. [10b] T. Kauffmann in Advances in Metal Carbene Chemistry (Ed.: U. Schubert), Kluwer Academic Publishers, Dordrecht, 1989, 359-378.
14. [10c] T. Kauffmann in Organometallics in Organic Synthesis 2 (Eds: H. Werner, G. Erker), Springer, Berlin, 1989, 161-183.
15. [11a] J. Furukawa, N. Kawabata, J. Nishimura, Tetrahedron 1968, 24, 53-58.
16. [11b] S. Miyano, H. Hashimoto, J. Chem. Soc., Chem Commun. 1971, 1418-1420.
17. [11c] B. M. Trost, D. P. Curran, J. Am. Chem. Soc. 1981, 103, 7380-7381.
18. L. A. Paquette, A. M. Doherty, Polyquinane Chemistry, Springer, Berlin, 1987 and references cited therein.
19. L. Claisen, Chem. Ber. 1907, 40, 3903-3914.
20. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100846. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: (internat.) +44 (0)1223/ 336033, e-mail: deposit@chemcrys.cam.ac.uk).
21. D. L. J. Clive, Tetrahedron 1978, 34, 1049-1132.
22. T. J. Lee, J. Holtz, R. L. Smith, J. Org Chem. 1982, 47, 4750-4757.
23. [17a] K. Suzuki, K. Tomooka, T. Matsumoto, E. Katayama, G.-I. Tsuchihashi, Tetrahedron Lett. 1985, 26, 3711-3715.
24. [17b] S. Kobayashi, J. Shibata, M. Shimada, M. Ohno, Tetrahedron Lett. 1990, 31, 1577-1581.
25. E. Winterfeldt, Synthesis 1975, 617-630.
26. A. G. Brook, J. M. Duff, P. F. Jones, N. R. Davis, J. Am. Chem. Soc. 1967, 59, 431-434.
27. M. Mikolajczyk. S. Grzejszczak, A. Zatorski, B. Mlotkowska, H. Gross, B. Costisella, Tetrahedron 1978, 34, 3081-3088.
28. Interestingly, by the procedure described a mixture of 21a and 21b in a ratio of 18:1 was obtained. Upon sequential treatment of this mixture with n-BuLi and water the ratio of the isomers changed to 1:18. It seems that 21a is the product of a kinetically controlled reduction of 14a and that 21b is the thermodynamically more stable isomer, possibly because of an intramolecular hydrogen bond. The configuration at C-1 of 21a and 21b was determined by NOE experiments.
29. B.-T. Gröbel, D. Seebach, Synthesis 1977, 357-402.
30. E. J. Corey, D. J. Beames, J. Am Chem. Soc. 1973, 95, 5829-5831.
31. G. Stork, K. Zaho, Tetrahedron Lett. 1989, 30, 287-291.
32. [25a] H. J. Reich, J. M. Renga, J. Org. Chem. 1975, 40, 3313-3314.
33. [25b] M. Jefson, J. Meinwald, Tetrahedron Lett. 1981, 22, 3561-3564.
34. [26a] E. J. Corey, N. W. Gilman, B. E. Ganem, J. Am. Chem. Soc. 1968, 90, 5616-5617,
35. [26b] E. I Corey, J. A. Katzenellenbogen, N. W. Gilman, S. A. Roman, B. W. Erickson, J. Am. Chem. Soc. 1968, 90, 5618-5619.
36. [27a] K Mori, M. Tsuji. Tetrahedron 1988, 44, 2835-2842.
37. [27b] L. A. Paquette, G. D. Annis, H. Schostarez, J. Am. Chem. Soc. 1982, 104, 6646-6653.
38. [27a][27b].
39. T. Ohtsuka, H. Shirahama, T. Matsumoto, Tetrahedron Lett. 1983, 24, 3851-3854.
40. D. E. Cane, P. J. Thomas, J. Am. Chem. Soc. 1984, 106, 5295-5303.
41. R. K. L. Ossenkamp, H.-J. Gais, Liebigs Ann. 1997, 2433-2442.