A practical route to methyl nonactate

Chemical Communications

Volumn , Issue 3, 1996, Pages 431-432

  Metz, Peter ^a   Meiners, Uta ^a   Cramer, Eva ^a   Fröhlich, Roland ^a   Wibbeling, Birgit ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

NONACTIC ACID METHYL ESTER; NONACTIN; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTALLOGRAPHY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030060856     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960000431     Document Type: Article

References (44)

1. For reviews, see: W. Keller-Schierlein and H. Gerlach, Fortschr. Chem. Org. Naturst., 1968, 26, 161; Y. Nawata, K. Ando and Y. Iitaka, Met. Ions Biol. Syst., 1985, 19, 207.
2. For reviews, see: W. Keller-Schierlein and H. Gerlach, Fortschr. Chem. Org. Naturst., 1968, 26, 161; Y. Nawata, K. Ando and Y. Iitaka, Met. Ions Biol. Syst., 1985, 19, 207.
3. Use in biosensors: S. B. Butt and K. Cammann, Anal. Lett., 1992, 25, 1597.
4. M. V. Nefelova and A. N. Sverdlova, Antibiot. Med. Biotekhnol., 1985, 30, 261.
5. H. Oishi, T. Sugawa, T. Okutomi, K. Suzuki, T. Hayashi, M. Sawada and K. Ando, J. Antibiot., 1970, 23, 105; L. P. Shopotova and Y. D. Shenin, Zh. Prikl. Khim. (Leningrad), 1993, 66, 1334.
6. H. Oishi, T. Sugawa, T. Okutomi, K. Suzuki, T. Hayashi, M. Sawada and K. Ando, J. Antibiot., 1970, 23, 105; L. P. Shopotova and Y. D. Shenin, Zh. Prikl. Khim. (Leningrad), 1993, 66, 1334.
7. D. M. Callewaert, G. Radcliff, Y. Tanouchi and H. Shichi, Immunopharmacology, 1988, 16, 25; Y. Tanouchi and H. Shichi, Immunology, 1988, 63, 471.
8. D. M. Callewaert, G. Radcliff, Y. Tanouchi and H. Shichi, Immunopharmacology, 1988, 16, 25; Y. Tanouchi and H. Shichi, Immunology, 1988, 63, 471.
9. Studies on the biosynthesis: P. Stahl and H. Pape, Arch. Mikrobiol., 1972, 85, 239; D. M. Ashworth, C. A. Clark and J. A. Robinson, J. Chem. Soc., Perkin Trans. 1, 1989, 1461; M. V. Nefelova, I. Y. Karelina, A. N. Sverdlova and N. S. Egorov, Biokhimiya, 1989, 54, 1873, Biochemistry (Eng. Transl.), 1990, 1531.
10. Studies on the biosynthesis: P. Stahl and H. Pape, Arch. Mikrobiol., 1972, 85, 239; D. M. Ashworth, C. A. Clark and J. A. Robinson, J. Chem. Soc., Perkin Trans. 1, 1989, 1461; M. V. Nefelova, I. Y. Karelina, A. N. Sverdlova and N. S. Egorov, Biokhimiya, 1989, 54, 1873, Biochemistry (Eng. Transl.), 1990, 1531.
11. Studies on the biosynthesis: P. Stahl and H. Pape, Arch. Mikrobiol., 1972, 85, 239; D. M. Ashworth, C. A. Clark and J. A. Robinson, J. Chem. Soc., Perkin Trans. 1, 1989, 1461; M. V. Nefelova, I. Y. Karelina, A. N. Sverdlova and N. S. Egorov, Biokhimiya, 1989, 54, 1873, Biochemistry (Eng. Transl.), 1990, 1531.
12. Studies on the biosynthesis: P. Stahl and H. Pape, Arch. Mikrobiol., 1972, 85, 239; D. M. Ashworth, C. A. Clark and J. A. Robinson, J. Chem. Soc., Perkin Trans. 1, 1989, 1461; M. V. Nefelova, I. Y. Karelina, A. N. Sverdlova and N. S. Egorov, Biokhimiya, 1989, 54, 1873, Biochemistry (Eng. Transl.), 1990, 1531.
13. (a) H. Gerlach, K. Oertle, A. Thalmann and S. Servi, Helv. Chim. Acta, 1975, 58, 2036;
14. (b) U. Schmidt, J. Gombos, E. Haslinger and H. Zak, Chem. Ber., 1976, 109, 2628;
15. (c) P. A. Bartlett, J. D. Meadows and E. Ottow, J. Am. Chem. Soc., 1984, 106, 5304;
16. (d) I. Fleming and S. K. Ghosh, J Chem. Soc., Chem. Commun., 1994, 2287;
17. (e) J. Y. Lee and B. H. Kim, Tetrahedron Lett., 1995, 36, 3361.
18. U. Schmidt and J. Werner, Synthesis, 1986, 986.
19. The actic acids 2 display insecticidal activity, too: J. Jizba, V. Přikrylová, L. Ujhelyiová and Š. Varkonda, Folia Microbiol., 1992, 37, 299. A macrodiolide of homononactic acid 2b acts as a fungicidal agent: H. R. Y. Jois, A. Sarkar and S. Gurusiddaiah, Antimicrob. Agents Chemother., 1986, 30, 458.
20. The actic acids 2 display insecticidal activity, too: J. Jizba, V. Přikrylová, L. Ujhelyiová and Š. Varkonda, Folia Microbiol., 1992, 37, 299. A macrodiolide of homononactic acid 2b acts as a fungicidal agent: H. R. Y. Jois, A. Sarkar and S. Gurusiddaiah, Antimicrob. Agents Chemother., 1986, 30, 458.
21. For recent syntheses of 2a, see: I. Fleming and S. K. Ghosh, J. Chem. Soc., Chem. Commun., 1994, 2285; M. Ahmar, C. Duyck and I. Fleming, Pure Appl. Chem., 1994, 66, 2049; G. Solladie and C. Dominguez, J. Org. Chem.. 1994, 59, 3898; see also ref. 7e.
22. For recent syntheses of 2a, see: I. Fleming and S. K. Ghosh, J. Chem. Soc., Chem. Commun., 1994, 2285; M. Ahmar, C. Duyck and I. Fleming, Pure Appl. Chem., 1994, 66, 2049; G. Solladie and C. Dominguez, J. Org. Chem.. 1994, 59, 3898; see also ref. 7e.
23. For recent syntheses of 2a, see: I. Fleming and S. K. Ghosh, J. Chem. Soc., Chem. Commun., 1994, 2285; M. Ahmar, C. Duyck and I. Fleming, Pure Appl. Chem., 1994, 66, 2049; G. Solladie and C. Dominguez, J. Org. Chem.. 1994, 59, 3898; see also ref. 7e.
24. A. Warm and P. Vogel, Helv. Chim. Acta, 1987, 70, 690.
25. R. D. Walkup and G. Park, J. Am. Chem. Soc., 1990, 112, 1597; B. Lygo, Tetrahedron, 1988, 44, 6889.
26. R. D. Walkup and G. Park, J. Am. Chem. Soc., 1990, 112, 1597; B. Lygo, Tetrahedron, 1988, 44, 6889.
27. (a) E. Bovenschulte, P. Metz and G. Henkel, Angew. Chem., Int. Ed. Engl., 1989, 28, 202;
28. (b) P. Metz and E. Cramer, Tetrahedron Lett., 1993, 34, 6371;
29. (c) P. Metz, U. Meiners, R. Fröhlich and M. Grehl, J. Org. Chem., 1994, 59, 3687;
30. (d) P. Metz, J. Stölting, M. Läge and B. Krebs, Angew. Chem., Int. Ed. Engl., 1994, 33, 2195;
31. (e) P. Metz, M. Fleischer and R. Fröhlich, Tetrahedron, 1995, 51, 711.
32. S. L. Schreiber, R. E. Claus and J. Reagan, Tetrahedron Lett., 1982, 23, 3867; O. Arjona, A. Martin-Domenech and J. Plumet, J. Org. Chem., 1993, 58, 7929.
33. S. L. Schreiber, R. E. Claus and J. Reagan, Tetrahedron Lett., 1982, 23, 3867; O. Arjona, A. Martin-Domenech and J. Plumet, J. Org. Chem., 1993, 58, 7929.
34. R. J. Ferrier and R. H. Furneaux, Carbohydr. Res., 1976, 52, 63; L. Chanteloup and J.-M. Beau, Tetrahedron Lett., 1992, 33, 5347.
35. R. J. Ferrier and R. H. Furneaux, Carbohydr. Res., 1976, 52, 63; L. Chanteloup and J.-M. Beau, Tetrahedron Lett., 1992, 33, 5347.
36. K. C. Nicolaou, C.-K. Hwang, B. E. Marron, S. A. DeFrees, E. A. Couladouros, Y. Abe, P. J. Carroll and J. P. Snyder, J. Am. Chem. Soc., 1990, 112, 3040.
37. L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131; T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992.
38. L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131; T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992.
39. (R)- and (S)-Epoxypropane: K. Rossen, P. M. Simpson and K. M. Wells, Synth. Commun., 1993, 23, 1071; M. K. Ellis and B. T. Golding, Org. Synth., 1985, 63, 140; (R)- and (S)-1,2-epoxybutane: U. Goergens and M. P. Schneider, Tetrahedron: Asymmetry, 1992, 3, 1149; H. K. Chenault, J. Dahmer and G. M. Whitesides, J. Am Chem. Soc., 1989, 111, 6354, for the synthesis of the (S)-enantiomer, see also ref. 8; (R)-1,2-epoxy-3-methylbutane: B. Koppenhoefer and V. Schurig, Org. Synth., 1988, 66, 160; (S)-1,2-epoxy-3-methylbutane: K. Tsuji, T. Hirano and T. Tsuruta, Makromol. Chem., 1975, Suppl. 1, 55.
40. (R)- and (S)-Epoxypropane: K. Rossen, P. M. Simpson and K. M. Wells, Synth. Commun., 1993, 23, 1071; M. K. Ellis and B. T. Golding, Org. Synth., 1985, 63, 140; (R)- and (S)-1,2-epoxybutane: U. Goergens and M. P. Schneider, Tetrahedron: Asymmetry, 1992, 3, 1149; H. K. Chenault, J. Dahmer and G. M. Whitesides, J. Am Chem. Soc., 1989, 111, 6354, for the synthesis of the (S)-enantiomer, see also ref. 8; (R)-1,2-epoxy-3-methylbutane: B. Koppenhoefer and V. Schurig, Org. Synth., 1988, 66, 160; (S)-1,2-epoxy-3-methylbutane: K. Tsuji, T. Hirano and T. Tsuruta, Makromol. Chem., 1975, Suppl. 1, 55.
41. (R)- and (S)-Epoxypropane: K. Rossen, P. M. Simpson and K. M. Wells, Synth. Commun., 1993, 23, 1071; M. K. Ellis and B. T. Golding, Org. Synth., 1985, 63, 140; (R)- and (S)-1,2-epoxybutane: U. Goergens and M. P. Schneider, Tetrahedron: Asymmetry, 1992, 3, 1149; H. K. Chenault, J. Dahmer and G. M. Whitesides, J. Am Chem. Soc., 1989, 111, 6354, for the synthesis of the (S)-enantiomer, see also ref. 8; (R)-1,2-epoxy-3-methylbutane: B. Koppenhoefer and V. Schurig, Org. Synth., 1988, 66, 160; (S)-1,2-epoxy-3-methylbutane: K. Tsuji, T. Hirano and T. Tsuruta, Makromol. Chem., 1975, Suppl. 1, 55.
42. (R)- and (S)-Epoxypropane: K. Rossen, P. M. Simpson and K. M. Wells, Synth. Commun., 1993, 23, 1071; M. K. Ellis and B. T. Golding, Org. Synth., 1985, 63, 140; (R)- and (S)-1,2-epoxybutane: U. Goergens and M. P. Schneider, Tetrahedron: Asymmetry, 1992, 3, 1149; H. K. Chenault, J. Dahmer and G. M. Whitesides, J. Am Chem. Soc., 1989, 111, 6354, for the synthesis of the (S)-enantiomer, see also ref. 8; (R)-1,2-epoxy-3-methylbutane: B. Koppenhoefer and V. Schurig, Org. Synth., 1988, 66, 160; (S)-1,2-epoxy-3-methylbutane: K. Tsuji, T. Hirano and T. Tsuruta, Makromol. Chem., 1975, Suppl. 1, 55.
43. (R)- and (S)-Epoxypropane: K. Rossen, P. M. Simpson and K. M. Wells, Synth. Commun., 1993, 23, 1071; M. K. Ellis and B. T. Golding, Org. Synth., 1985, 63, 140; (R)- and (S)-1,2-epoxybutane: U. Goergens and M. P. Schneider, Tetrahedron: Asymmetry, 1992, 3, 1149; H. K. Chenault, J. Dahmer and G. M. Whitesides, J. Am Chem. Soc., 1989, 111, 6354, for the synthesis of the (S)-enantiomer, see also ref. 8; (R)-1,2-epoxy-3-methylbutane: B. Koppenhoefer and V. Schurig, Org. Synth., 1988, 66, 160; (S)-1,2-epoxy-3-methylbutane: K. Tsuji, T. Hirano and T. Tsuruta, Makromol. Chem., 1975, Suppl. 1, 55.
44. (R)- and (S)-Epoxypropane: K. Rossen, P. M. Simpson and K. M. Wells, Synth. Commun., 1993, 23, 1071; M. K. Ellis and B. T. Golding, Org. Synth., 1985, 63, 140; (R)- and (S)-1,2-epoxybutane: U. Goergens and M. P. Schneider, Tetrahedron: Asymmetry, 1992, 3, 1149; H. K. Chenault, J. Dahmer and G. M. Whitesides, J. Am Chem. Soc., 1989, 111, 6354, for the synthesis of the (S)-enantiomer, see also ref. 8; (R)-1,2-epoxy-3-methylbutane: B. Koppenhoefer and V. Schurig, Org. Synth., 1988, 66, 160; (S)-1,2-epoxy-3-methylbutane: K. Tsuji, T. Hirano and T. Tsuruta, Makromol. Chem., 1975, Suppl. 1, 55.