Asymmetric synthesis of (+)- and (-)-streptenol A

European Journal of Organic Chemistry

Volumn , Issue 4, 1999, Pages 751-756

  Enders, Dieter ^a   Hundertmark, Thomas ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric synthesis; Natural products; SAMP RAMP hydrazones; Streptenol A; Synthetic methods

Indexed keywords

ALDEHYDE; DIOXANE DERIVATIVE; HYDRAZONE DERIVATIVE; STREPTENOL A; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032818398     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199904)1999:4<751::AID-EJOC751>3.0.CO;2-R     Document Type: Article

References (29)

1. [1a] W. Keller-Schierlein, D. Wuthier, H. Drautz, Helv. Chim. Acta 1983, 66, 1253.
2. [1b] Y. Romeyke, M. Keller, H. Kluge, S. Grabley, P. Hammann, Tetrahedron 1991, 47, 3335.
3. [1c] S. Grabley, P. Hammann, H. Kluge, J. Wink, J. Antibiotics 1991, 44, 797.
4. [1d] T. Takeuchi, M. Ishizuka, H. Otai, M. Hamada, Jpn. Kokais Tokkyo, Koho JP 01,206,96 [89,206,996], 1989 [Chem. Abstr. 1990, 112, 75317y].
5. [1d] T. Takeuchi, M. Ishizuka, H. Otai, M. Hamada, Jpn. Kokais Tokkyo, Koho JP 01,206,96 [89,206,996], 1989 [Chem. Abstr. 1990, 112, 75317y].
6. [1e] A. Arone, R. Cardillo, G. Nasini, O. Vajna de ava, S. Quaroni, Phytochemistry 1988, 27, 3611.
7. S. Mizutani, H. Odai, T. Masuda, M. Iijima, M. Osono, M. Hamada, H. Naganawa, M. Ishizuka, T. Takeuchi, J. Antibiotics 1989, 42, 952.
8. J. Adam, R. Klein, S. Grabley, P. Hammann, Tetrahedron 1995, 51, 8247.
9. [4a] M. Franck-Neumann, P. Bissinger, P. Geoffroy Tetrahedron Lett. 1995, 38, 4469.
10. [4b] M. Hayashi, H. Kaneda, N. Oguni, Tetrahedron: Asymmetry 1995, 6, 2511.
11. S. Blechert, H. Dollt, Liebigs Ann. 1996, 2135.
12. [6a] P. D. Theisen, C. H. Heathcock, J. Org. Chem 1988, 53, 2374.
13. [6b] P. D. Theisen, C. H. Heathcock, J. Org. Chem. 1993, 55, 142.
14. [7a] D. H. R. Barton, S. W. J. McCombie, J. Chem. Soc., Perkin Trans. 1 1975, 1574.
15. [7b] D. Enders, T. Hundertmark, C. Lampe, U. Jegelka, I. Scharfbillig, Eur. J. Org. Chem. 1998, 2839.
16. [8a] D. Enders, B. Bockstiegel, Synthesis 1989, 493.
17. [8b] D. Enders, W. Gatzweiler, U. Jegelka, Synthesis 1991, 1137.
18. [8c] D. Enders, O. F. Prokopenko, Liebigs Ann. 1995, 1185.
19. [8d] M. Majewski, P. Nowak, Tetrahedron: Asymmetry 1998, 9, 2611.
20. D. Enders, T. Hundertmark, R. Lazny, Synlett 1998, 721.
21. [10a] D. E. ward, C. K. Ree, Tetrahedron Lett 1991, 34, 7165.
22. [10b] J. A. Dale, D. L. Dull, S. H. Mosher, J. Org. Chem. 1969, 34, 2543.
23. [10c] J. A. Dale, S. H. Mosher, J. Am. Chem. Soc. 1973, 95, 512.
24. [11a] W. P. Griffith, S. V. Ley, G. P. Whitecombe, A. D. White, J. Chem. Soc., Chem. Commun. 1989, 1625.
25. [11b] S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
26. E. J. Corey, J. W. Suggs, Tetrahedron Lett. 1975, 2647.
27. Y. Leblanc, B. J. Fitzsimmons, J. Adams, F. Perez, J. Org. Chem. 1986, 51, 789.
28. D. Hoppe, H. Schmincke, H. - W. Kleemann, Tetrahedron 1989, 45, 687.
29. J. Vader, H. Sengers, A. de Groot, Tetrahedron 1989, 45, 2131.