Bryophyte constituents; 6: Synthesis of herbertene-derived sesquiterpenes from Herberta adunca

Synthesis

Volumn , Issue 7, 1996, Pages 863-870

  Eicher, Theophil ^a   Servet, Frank ^a   Speicher, Andreas ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

baker's yeast; bryophyte constituents; enantioselective synthesis; herbertene; sesquiterpenes

Indexed keywords

ALPHA HERBERTENOL; BETA HERBERTENOL; HERBERTENOLIDE; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030004137     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4309     Document Type: Article

References (29)

1. Matsuo, A.; Yuki, S.; Nakayama, M.; Hayashi, S. J. Chem. Soc., Chem. Commun. 1981, 864.
2. Matsuo, A.; Yuki, S.; Nakayama, M.; Hayashi, S. Chem. Lett. 1982, 463.
3. Fukuyama, Y.; Asakawa, Y. J. Chem. Soc., Perkin Trans, 1 1991, 2737.
4. Matsuo, A.; Yuki, S.; Nakayama, M. Chem. Lett. 1983, 1041.
5. (a) Leriverend, M.-L.; Vazeux, M. J. Chem. Soc., Chem. Commun. 1982, 866.
6. (b) Takano, S.; Moriya, M.; Ogasawara, K. Tetrahedron Lett. 1992, 33, 329.
7. (c) Saha, A. K.; Das, S.; Mukherjee, D.; Fronczek, F.R. Tetrahedron Lett. 1994, 35, 3353.
8. (a) Zinsmeister, H. D.; Becker, H.; Eicher, T. Angew. Chem. 1991, 103, 134; Angew. Chem., Int. Ed. Engl. 1991, 30, 130.
9. (a) Zinsmeister, H. D.; Becker, H.; Eicher, T. Angew. Chem. 1991, 103, 134; Angew. Chem., Int. Ed. Engl. 1991, 30, 130.
10. (b) Speicher, A.; Eicher, T. Synthesis 1995, 998.
11. Sato, K.; Suzuki, S.; Kojima, Y. J. Org. Chem. 1967, 32, 339.
12. Koenig, K.E.; Lein, G.M.; Stuckler, P.; Kaneda, T.; Cram, D. J. J. Am. Chem. Soc: 1979, 101, 3553.
13. Bird, C. W.; Yeong, Y. C. Synthesis 1974, 27.
14. Yamada, K.; Yazawa, H.; Uemura, D.; Toda, M.; Hirata, Y. Tetrahedron 1969, 25, 3509.
15. (a) Roesen, W. E.; Dorfman, L.; Linfield, M. P. J. Org. Chem. 1964, 29, 1723.
16. (b) Balsamo, A.; Berti, G.; Crotti, P.; Ferretti, M.; Macchia, B.; Macchia, F. J. Org. Chem. 1974, 39, 2596.
17. We thank Dr. V. Huch and Prof. Dr. M. Veith, Fachbereich Anorganische Chemie, Universität des Saarlandes for performing X-ray analyses of compounds 15 and 2.
18. Matsuo, A.; Yuki, S.; Nakayama, M. J. Chem. Soc., Perkin Trans, 1 1986, 701.
19. (a) Saigo, K.; Koda, H.; Nohira, H. Bull. Chem. Soc. Jpn. 1979, 52, 3119.
20. (b) Valli, V. L. K.; Sarma, G. V. M.; Choudary, B. M. Ind. J. Chem. 1990, 29B, 481.
21. (c) The synthesis of methyl (1S)- and (1R)-1-methyl-2-oxo-cyclopentanecarboxylate (99/92% ce) was reported: Kato, K.; Suemune, H.; Sakai, K. Tetrahedron 1994, 50, 3315. In our hands the method applied did not prove to be suitable for the preparation of (S)-9 in a preparative scale.
22. Sato, T.; Maeno, H.; Noro, T.; Fujisawa, J. Chem. Lett. 1988, 1739.
23. Enders, D.; Zamponi, A.; Schäfer, T.; Nübling, C.; Eichenauer, H.; Sitki Demir, A.; Raabe, G. Chem. Ber. 1994, 127, 1707.
24. Frater, G. Helv. Chim. Acta 1980, 63, 1383.
25. Frater, G. Helv. Chim. Acta 1979, 62, 2825, 2829.
26. Orth, U.; Pfeiffer, H.-P.; Breitmaier, E. Chem. Ber. 1986, 119, 3507.
27. Wolff-Kishner procedure at more than 215 C induced cleavage of the methyl ether.
28. Nasipuri, D.; Roy, D.N. J. Ind. Chem. Soc. 1963, 40, 334.
29. Seebach, D.; Roggo, D.; Maetzke, T. Helv. Chim. Acta 1987, 70, 1605.