Isolation, identification, and enantioselective synthesis of octane- 1,3,7-triol: Determination of its absolute configuration

Journal of Natural Products

Volumn 62, Issue 1, 1999, Pages 35-40

  Beuerle, Till ^a   Engelhard, Sonja ^a   Bicchi, Carlo ^b   Schwab, Wilfried ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTANEDIOL; ALCOHOL DERIVATIVE; ALKANE DERIVATIVE; ANTIINFECTIVE AGENT; BUTANE 1,2,4 TRIOL; OCTANE 1,3 DIOL; OCTANE 1,3,7 TRIOL; UNCLASSIFIED DRUG; VOLATILE AGENT;

ACETYLATION; APPLE; ARTICLE; DRUG CONFORMATION; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG SYNTHESIS; ENANTIOMER; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; SOLID PHASE EXTRACTION;

EID: 0032940856     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np980094e     Document Type: Article

References (38)

1. Frankenfeld, J. W.; Karel, M.; Labuza, T. P.; Sinskey, A. J. United States Patent, 3,806,615, Apr 23, 1974.
2. Wright, D. L.; Frankenfeld, J. W. United States Patent, 3,836,672, Sep 17, 1974.
3. Frankenfeld, J. W.; Mohan, R. R.; Squibb, R. L. United States Patent, 3,773,518, Nov 20, 1973.
4. Frankenfeld, J. W.; Karel, M.; Labuza, T. P. United States Patent, 3,732,112, May 8, 1973.
5. Akedo, M.; Sinskey, A. J.; Gomez, R. J. Food Sci. 1977, 42, 699-706.
6. Dymsza, H. A. Fed Proc. 1975, 34, 2167-2170.
7. Brulé, G. Ann. Technol. Agric. 1973, 22, 45-58.
8. Yajima, I.; Yanai, T.; Nakamura, M.; Sakakibara, H.; Hayashi, K. Agric. Biol Chem. 1984, 48, 849-855.
9. Schwab, W.; Scheller, G.; Gerlach, D.; Schreier, P. Phytochemistry 1989, 28, 157-160.
10. Beuerle, T.; Schreier, P.; Schwab, W. Nat. Prod. Lett. 1997, 10, 119-124.
11. Beuerle, T.; Schreier, P.; Brunerie, P.; Bicchi, C.; Schwab, W. Phytochemistry 1996, 43, 145-149.
12. Berger, R. G.; Dettweiler, G. R.; Drawert, F. Dt. Lebensm.-Rundschau 1988, 84, 344-347.
13. Beuerle, T.; Schwab, W. Phytochemistry 1997, 45, 1153-1155.
14. Taber, D. F.; Amedio, J. J.; Raman, K. J. Org. Chem. 1988, 53, 2984-2990.
15. Tsuji, J.; Nagashima, H.; Nemoto, H. Org. Synth. 1984, 62, 9-13.
16. Tsuji, J. Synthesis 1984, 369-384.
17. The changed stereochemical descriptor at C-7 is due to the changing substituent priorities according to the Cahn-Ingold-Prelog system, not to an inversion of stereochemistry.
18. Nájera, C.; Yus, M.; Seebach, D. Helv. Chim. Acta 1984, 67, 289-300.
19. Voss, G.; Gerlach, H. Helv. Chim. Acta 1983, 66, 2294-2307.
20. Czernecki, S.; Georgoulis, C.; Provelenghiou, C. Tetrahedron Lett. 1976, 39, 3535-3536.
21. Martin, J. C.; Smee, D. F.; Verdeyden, J. P. H. J. Org. Chem. 1985, 50, 755-759.
22. Meyers, A. I.; Lawson, J. P. Tetrahedron Lett. 1982, 23, 4883-4886.
23. Ho, P.-T. Tetrahedron Lett. 1978, 19, 1623-1626.
24. Liu, C.; Coward, J. K. J. Org. Chem. 1991, 56, 2262-2264.
25. Single, J. D.; Huang, T. T.-S.; Franzus, B. J. Org. Chem. 1981, 46, 3526-3530.
26. Liu, C.; Coward, J. K. J. Med. Chem. 1991, 34, 2094-2101.
27. Fujioka, H.; Kitagawa, H.; Nagatomi, Y.; Kita, Y. J. Org. Chem. 1996, 81, 7309-7315.
28. Alborn, H. T.; Turlings, T. C.; Jones, T. H.; Stenhagen, G.; Loughrin, J. H.; Tumlinson, J. H. Science 1997, 945-948.
29. Baugh, P. J. Gas Chromatography; Oxford University Press: New York, 1993; pp 12-17.
30. Samain, D.; Descoins, C. Synthesis 1978, 388-389.
31. Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755-760.
32. Tércio, J.; Ferreira, B.; Simonelli, F. Tetrahedron 1990, 46, 6311-6318.
33. Nakatsuka, T.; Iwata, H.; Tanaka, R.; Imajo, S.; Ishiguro, M. J. Chem. Soc., Chem. Commun. 1991, 662-664.
34. Homer, L.; Schmitt, R. E. Phosphorus Sulfur 1982, 13, 189-211.
35. Wang, X. J. Chem. Soc., Chem. Commun. 1991, 1515-1517.
36. Mori, K.; Takigawa, T.; Matsuo, T. Tetrahedron 1979, 35, 933-940.
37. Kocienski, P. J.; Yeates, C.; Street, S. D. A.; Campbell, S. F. J. Chem. Soc., Perkin Trans, 1 1987, 2183-2187.
38. Van der Eycken, E.; De Wilde, H.; Deprez, L.; Vandewalle, M. Tetrahedron Lett. 1987, 28, 4759-4760.