A short asymmetric synthesis of both enantiomers of ramulosin and its analogues

Synthesis

Volumn , Issue 2, 1996, Pages 209-214

  Enders, Dieter ^a   Kaiser, Anja ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; ISOCOUMARIN DERIVATIVE; RAMULOSIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029968678     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4195     Document Type: Article

References (34)

1. Stodola, F.H.; Cabot, C.; Benjamin, C.R. Biochem. J. 1964, 93, 92.
2. Hendershot, W.F.; Hesseltine, C.W.; Pridham, T.G.; Benedict, T.G.; Jackson, R.W. Arch. Biochem. Biophys. 1962, 96, 166.
3. Tanenbaum, S.W.; Agarwal, S.C.; Williams, T.; Pitcher, R.G. Tetrahedron Lett. 1970, 2377.
4. Findlay, J.A.; Matsoukas, J.M:, Krepinsky, J. Can. J. Chem. 1976, 54, 3419.
5. Cordova, R.; Snider, B.B. Tetrahedron Lett. 1984, 25, 2945. Pietrusiewicz, K.M.; Salamonczyk, I. J. Org. Chem. 1988, 53, 2837. Vogt, K.; Schmidt, R.R. Tetrahedron 1988, 44, 3271.
6. Cordova, R.; Snider, B.B. Tetrahedron Lett. 1984, 25, 2945. Pietrusiewicz, K.M.; Salamonczyk, I. J. Org. Chem. 1988, 53, 2837. Vogt, K.; Schmidt, R.R. Tetrahedron 1988, 44, 3271.
7. Cordova, R.; Snider, B.B. Tetrahedron Lett. 1984, 25, 2945. Pietrusiewicz, K.M.; Salamonczyk, I. J. Org. Chem. 1988, 53, 2837. Vogt, K.; Schmidt, R.R. Tetrahedron 1988, 44, 3271.
8. Mori, K.; Gupta, A.K. Tetrahedron 1985, 41, 5295.
9. Takano, S.; Shimazaki, Y.; Ogasawara, K. Heterocycles 1989, 29, 2101.
10. Asaoka, M.; Sonoda, S.; Takei, H. Chem. Lett. 1989, 1847. Asaoka, M.; Sonoda, S.; Takei, S. Tetrahedron 1990, 46, 1541.
11. Asaoka, M.; Sonoda, S.; Takei, H. Chem. Lett. 1989, 1847. Asaoka, M.; Sonoda, S.; Takei, S. Tetrahedron 1990, 46, 1541.
12. Enders, D. In Asymmetric Synthesis, Vol. 3; Morrison, J.D., Ed.; Academic Press: Orlando, 1984; p 275. Enders, D. Chem. Scripta 1985, 25, 139. Enders, D.; Klatt, M. in Encyclopedia of Reagents of Organic Synthesis; Paquette, L.A., Ed.; Wiley: New York, 1995; in press.
13. Enders, D. In Asymmetric Synthesis, Vol. 3; Morrison, J.D., Ed.; Academic Press: Orlando, 1984; p 275. Enders, D. Chem. Scripta 1985, 25, 139. Enders, D.; Klatt, M. in Encyclopedia of Reagents of Organic Synthesis; Paquette, L.A., Ed.; Wiley: New York, 1995; in press.
14. Enders, D. In Asymmetric Synthesis, Vol. 3; Morrison, J.D., Ed.; Academic Press: Orlando, 1984; p 275. Enders, D. Chem. Scripta 1985, 25, 139. Enders, D.; Klatt, M. in Encyclopedia of Reagents of Organic Synthesis; Paquette, L.A., Ed.; Wiley: New York, 1995; in press.
15. Corey, E.J.; Enders, D. Chem. Ber. 1978, 111, 1362.
16. Enders, D.; Scherer, H.J.; Runsink, J. Chem. Ber. 1993, 126, 1929. Enders, D.; Scherer, H.J.; Raabe, G. Angew. Chem. 1991, 103, 1676; Angew. Chem., Int. Ed. Engl. 1991, 30, 1664.
17. Enders, D.; Scherer, H.J.; Runsink, J. Chem. Ber. 1993, 126, 1929. Enders, D.; Scherer, H.J.; Raabe, G. Angew. Chem. 1991, 103, 1676; Angew. Chem., Int. Ed. Engl. 1991, 30, 1664.
18. Enders, D.; Scherer, H.J.; Runsink, J. Chem. Ber. 1993, 126, 1929. Enders, D.; Scherer, H.J.; Raabe, G. Angew. Chem. 1991, 103, 1676; Angew. Chem., Int. Ed. Engl. 1991, 30, 1664.
19. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967. Enders, D.; Papadopoulos, K.; Rendenbach, B.E.M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 27, 3491. Enders, D.; Rendenbach, B.E.M. Tetrahedron 1986, 42, 2235. Enders, D.; Demir, A.S.; Rendenbach, B.E.M. Chem. Ber. 1987, 120, 1731. Enders, D.; Demir, A.S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795. Enders, D.; Müller, S.; Demir, A.S. Tetrahedron Lett. 1988, 29, 6437. Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821. Enders, D.; Wahl, H.; Papadopoulos, K. Liebigs Ann. 1995, 1177.
20. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967. Enders, D.; Papadopoulos, K.; Rendenbach, B.E.M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 27, 3491. Enders, D.; Rendenbach, B.E.M. Tetrahedron 1986, 42, 2235. Enders, D.; Demir, A.S.; Rendenbach, B.E.M. Chem. Ber. 1987, 120, 1731. Enders, D.; Demir, A.S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795. Enders, D.; Müller, S.; Demir, A.S. Tetrahedron Lett. 1988, 29, 6437. Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821. Enders, D.; Wahl, H.; Papadopoulos, K. Liebigs Ann. 1995, 1177.
21. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967. Enders, D.; Papadopoulos, K.; Rendenbach, B.E.M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 27, 3491. Enders, D.; Rendenbach, B.E.M. Tetrahedron 1986, 42, 2235. Enders, D.; Demir, A.S.; Rendenbach, B.E.M. Chem. Ber. 1987, 120, 1731. Enders, D.; Demir, A.S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795. Enders, D.; Müller, S.; Demir, A.S. Tetrahedron Lett. 1988, 29, 6437. Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821. Enders, D.; Wahl, H.; Papadopoulos, K. Liebigs Ann. 1995, 1177.
22. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967. Enders, D.; Papadopoulos, K.; Rendenbach, B.E.M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 27, 3491. Enders, D.; Rendenbach, B.E.M. Tetrahedron 1986, 42, 2235. Enders, D.; Demir, A.S.; Rendenbach, B.E.M. Chem. Ber. 1987, 120, 1731. Enders, D.; Demir, A.S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795. Enders, D.; Müller, S.; Demir, A.S. Tetrahedron Lett. 1988, 29, 6437. Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821. Enders, D.; Wahl, H.; Papadopoulos, K. Liebigs Ann. 1995, 1177.
23. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967. Enders, D.; Papadopoulos, K.; Rendenbach, B.E.M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 27, 3491. Enders, D.; Rendenbach, B.E.M. Tetrahedron 1986, 42, 2235. Enders, D.; Demir, A.S.; Rendenbach, B.E.M. Chem. Ber. 1987, 120, 1731. Enders, D.; Demir, A.S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795. Enders, D.; Müller, S.; Demir, A.S. Tetrahedron Lett. 1988, 29, 6437. Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821. Enders, D.; Wahl, H.; Papadopoulos, K. Liebigs Ann. 1995, 1177.
24. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967. Enders, D.; Papadopoulos, K.; Rendenbach, B.E.M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 27, 3491. Enders, D.; Rendenbach, B.E.M. Tetrahedron 1986, 42, 2235. Enders, D.; Demir, A.S.; Rendenbach, B.E.M. Chem. Ber. 1987, 120, 1731. Enders, D.; Demir, A.S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795. Enders, D.; Müller, S.; Demir, A.S. Tetrahedron Lett. 1988, 29, 6437. Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821. Enders, D.; Wahl, H.; Papadopoulos, K. Liebigs Ann. 1995, 1177.
25. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967. Enders, D.; Papadopoulos, K.; Rendenbach, B.E.M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 27, 3491. Enders, D.; Rendenbach, B.E.M. Tetrahedron 1986, 42, 2235. Enders, D.; Demir, A.S.; Rendenbach, B.E.M. Chem. Ber. 1987, 120, 1731. Enders, D.; Demir, A.S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795. Enders, D.; Müller, S.; Demir, A.S. Tetrahedron Lett. 1988, 29, 6437. Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821. Enders, D.; Wahl, H.; Papadopoulos, K. Liebigs Ann. 1995, 1177.
26. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967. Enders, D.; Papadopoulos, K.; Rendenbach, B.E.M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 27, 3491. Enders, D.; Rendenbach, B.E.M. Tetrahedron 1986, 42, 2235. Enders, D.; Demir, A.S.; Rendenbach, B.E.M. Chem. Ber. 1987, 120, 1731. Enders, D.; Demir, A.S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795. Enders, D.; Müller, S.; Demir, A.S. Tetrahedron Lett. 1988, 29, 6437. Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821. Enders, D.; Wahl, H.; Papadopoulos, K. Liebigs Ann. 1995, 1177.
27. Enders, D.; Kaiser, A. unpublished results.
28. When our work was finished, Urban et al. published an alternative asymmetric synthesis of 6-substituted 2-oxocyclohexanecarboxylates: Urban, E.; Riehs, G.; Knühl, G. Tetrahedron Lett. 1995, 36, 4773.
29. Enders, D.; Eichenauer, H. Chem. Ber. 1979, 122, 2933. Enders, D.; Fey, P.; Kipphardt, H. Org. Prep. Proceed. Int. 1985, 17, 1. Enders, D.; Frey, P.; Kipphardt, H. Org. Synth. 1987, 65, 173, 183.
30. Enders, D.; Eichenauer, H. Chem. Ber. 1979, 122, 2933. Enders, D.; Fey, P.; Kipphardt, H. Org. Prep. Proceed. Int. 1985, 17, 1. Enders, D.; Frey, P.; Kipphardt, H. Org. Synth. 1987, 65, 173, 183.
31. Enders, D.; Eichenauer, H. Chem. Ber. 1979, 122, 2933. Enders, D.; Fey, P.; Kipphardt, H. Org. Prep. Proceed. Int. 1985, 17, 1. Enders, D.; Frey, P.; Kipphardt, H. Org. Synth. 1987, 65, 173, 183.
32. Brenner, J.E. J. Org. Chem. 1961, 26, 22. Funk, R.L.; Fitzgerald, J.F.; Olmstead, T.A.; Para, K.S.; Wos, J.A. J. Am. Chem. Soc. 1993, 115, 8849. Sterzycki, R. Synthesis 1979, 724.
33. Brenner, J.E. J. Org. Chem. 1961, 26, 22. Funk, R.L.; Fitzgerald, J.F.; Olmstead, T.A.; Para, K.S.; Wos, J.A. J. Am. Chem. Soc. 1993, 115, 8849. Sterzycki, R. Synthesis 1979, 724.
34. Brenner, J.E. J. Org. Chem. 1961, 26, 22. Funk, R.L.; Fitzgerald, J.F.; Olmstead, T.A.; Para, K.S.; Wos, J.A. J. Am. Chem. Soc. 1993, 115, 8849. Sterzycki, R. Synthesis 1979, 724.