A general route to the monomeric subunits of the macrotetrolides - A short synthesis of methyl nonactate

European Journal of Organic Chemistry

Volumn , Issue 10, 1998, Pages 2073-2078

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

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Actic acids; Desulfurization; Heterocycles; Intramolecular Diels Alder reaction; Ksultones

Indexed keywords

EID: 0002018106     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199810)1998:10<2073::AID-EJOC2073>3.0.CO;2-D     Document Type: Article

References (61)

1. [1a] W Keller-Schierlein, H. Gerlach, Fortschr. Chem. Org. Naturst. 1968, 26, 161-189.
2. [1b] Y. Nawata, K. Ando, Y. Iitaka, Met. Ions Biol Syst. 1985, 19, 207-227.
3. [1c] Z. Zizka, Folia Microbiol 1998, 43, 7-14.
4. Use in biosensors: S. B. Butt, K. Cammann, Anal. Lett. 1992, 25, 1597-1615.
5. M. V. Nefelova, A. N. Sverdlova, Antibiot. Med. Biotekhnol. 1985, 30, 261-264; Chem. Abstr. 1985, 102, 201065.
6. M. V. Nefelova, A. N. Sverdlova, Antibiot. Med. Biotekhnol. 1985, 30, 261-264; Chem. Abstr. 1985, 102, 201065.
7. [4a] H. Oishi, T. Sugawa, T. Okutomi, K. Suzuki, T. Hayashi, M. Sawada, K. Ando, J. Antibiot. 1970, 23, 105-106.
8. [4b] L. P. Shopotova, Y. D. Shenin, Zh. Prikl. Khim. 1993, 66, 1334-1338: Chem. Abstr. 1994, 120, 158329.
9. [4b] L. P. Shopotova, Y. D. Shenin, Zh. Prikl. Khim. 1993, 66, 1334-1338: Chem. Abstr. 1994, 120, 158329.
10. [5a] D. M. Callewaert, G. Radcliff, Y. Tanouchi, H. Shichi, Immunopharmacology 1988, 16, 25 -32.
11. [5b] Y. Tanouchi, H. Shichi, Immunology 1988, 63, 471-475.
12. [6a] P. Stahl, H. Pape, Arch. Mikrobiol. 1972, 85, 239-248.
13. [6b] D. M. Ashworth, C. A. Clark, J. A. Robinson, J. Chem. Soc., Perkin Trans. 1 1989, 1461-1467.
14. [6c] M. V. Nefelova, I. Y. Karelina, A. N. Sverdlova, N. S. Egorov, Biokhimiya 1989, 54, 1873-1880, English translation: Biochemistry 1990, 1531-1538.
15. [6c] M. V. Nefelova, I. Y. Karelina, A. N. Sverdlova, N. S. Egorov, Biokhimiya 1989, 54, 1873-1880, English translation: Biochemistry 1990, 1531-1538.
16. [6d] J. Jizba, M. Heidukova. E. Prokinova, Biotechnol. Lett. 1997, 19, 295-297.
17. [6e] M. J. Earle, N. D. Priestley, Bioorg. Med. Chem. Left. 1997, 7, 2187-2192.
18. [7a] H. Gerlach, K. Oertle, A. Thalmann, S. Servi, Helv. Chim. Acta 1975, 58, 2036-2043.
19. [7b] U. Schmidt, J. Gombos, E. Haslinger, H. Zak, Chem. Ber. 1976, 109, 2628-2644.
20. [7c] P. A. Bartlett, J. D. Meadows, E. Ottow, J. Am Chem. Soc. 1984, 106, 5304-5311.
21. [7d] I. Fleming, S. K. Ghosh, J. Chem. Soc., Chem. Commun. 1994, 2287-2288.
22. [7e] J. Y. Lee, B. H. Kim, Tetrahedron 1996, 52, 571 -588.
23. U. Schmidt, J. Werner, Synthesis 1986, 986-992.
24. [9a] The actic acids 2 display msecticidal activity, too: J. Jizba, V. Prikrylová, L. Ujhelyiová, S. Varkonda, Folia Microbiol. 1992, 37, 299-303.
25. [9b] A macrodiolide of homononactic acid (2b) acts as a fungicidal agent: H. R. Y. Jois, A. Sarkar, S. Gurusiddaiah, Antimicrob. Agents Chemother. 1986, 30, 458-464.
26. [10a] I. Fleming, S. K. Ghosh, Stud. Nat. Prod. Chem. 1996, 18, 229-268.
27. [10b] K. Takatori, K. Tanaka, K. Matsuoka. K. Morishita, M. Kajiwara, Synlett 1997, 159-160.
28. [10c] G. Mandville, C. Girard, R. Bloch, Tetrahedron 1997, 53, 17079-17088.
29. [11a] B. Lvgo, Tetrahedron 1988, 44, 6889-6896.
30. [11b] R. D. Walkup, G. Park, J Am Chem. Soc. 1990, 112, 1597-1603.
31. P. Metz, U. Meiners, E. Cramer, R. Fröhlich, B. Wibbeling, Chem. Commun. 1996, 431-432.
32. P. Metz, J. Prakt, Chem. 1998, 340, 1-10.
33. E. Bovenschulte, P. Metz, G. Henkel, Angew Chem. 1989, 101, 204-206; Angew. Chem. Int. Ed. Engl. 1989, 28, 202-203.
34. E. Bovenschulte, P. Metz, G. Henkel, Angew Chem. 1989, 101, 204-206; Angew. Chem. Int. Ed. Engl. 1989, 28, 202-203.
35. P. Metz, U Meiners. R. Fröhlich, M. Grehl, J. Org. Chem. 1994, 59, 3687-3689.
36. [16a] P. Metz, E. Cramer, Tetrahedron Lett. 1993, 34, 6371-6374.
37. [16b] P. Metz, J. Stölting, M. Läge, B. Krebs, Angew. Chem. 1994, 106. 2275-2276; Angew. Chem. Int. Ed. Engl. 1994, 33, 2195-2197.
38. [16b] P. Metz, J. Stölting, M. Läge, B. Krebs, Angew. Chem. 1994, 106. 2275-2276; Angew. Chem. Int. Ed. Engl. 1994, 33, 2195-2197.
39. -3. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101756. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 IEZ, UK [Fax: Int. code + 44(0)1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
40. [18a] S. L. Schreiber, R. E. Claus, J. Reagan, Tetrahedron Lett 1982, 23, 3867-3870.
41. [18b] R. E. Claus, S. L. Schreiber, Org. Synth. 1986, 64, 150-156.
42. [18c] O. Arjona, A. Martin-Domenech, J. Plumet, J. Org. Chem. 1993, 58, 7929-7931.
43. [19a] R. J. Ferrier, R. H. Furneaux, Carbohydr. Res. 1976, 52, 63-68.
44. [19b] L. Chanteloup. J.-M. Beau, Tetrahedron Lett. 1992, 33, 5347-5350.
45. R Mozingo, Org. Synthesis 1955, Coll. Vol. III, 181-183.
46. K. C. Nicolaou, C.-K. Hwang, B. E. Marron, S. A. DeFrees, E. A. Couladouros, Y. Abe, P. J. Carroll, J. P. Snyder, J. Am. Chem. Soc. 1990, 112, 3040-3054.
47. A. Warm, P. Vogel, Helv. Chim. Acta 1987, 70, 690-700.
48. [23a] T.-L. Ho, Tandem Organic Reactions, Wiley. New York, 1992.
49. [23b] L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
50. [23b] L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
51. [23c] L. F. Tietze, Chem. Ind. 1995, 453-457.
52. [23d] L. F. Tietze, Chem. Rev. 1996, 96, 115-136.
53. [24a] (R)- and (S)-Epoxypropane: M. K. Ellis, B. T. Golding, Org. Synth. 1985, 63, 140-146. - K. Rossen, P. M. Simpson, K. M.Wells, Synth. Commun 1993,23, 1071-1074.
54. [24a] (R)- and (S)-Epoxypropane: M. K. Ellis, B. T. Golding, Org. Synth. 1985, 63, 140-146. - K. Rossen, P. M. Simpson, K. M.Wells, Synth. Commun 1993,23, 1071-1074.
55. [8].
56. [8].
57. [24c] (R)-1,2-Epoxy-3-methylbutane: B. Koppenhoefer, V. Schurig, Org. Synth. 1988, 66, 160-172.
58. [24d] (S)-1,2-Epoxy-3-methylbutane: K. Tsuji, T. Hirano, T. Tsuruta, Makromol. Chem. 1975, Suppl. 1, 55-70.
59. For an efficient kinetic resolution of racemic terminal epoxides, see: M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938.
60. P. Metz, B. Hungerhoff, J. Org. Chem. 1997, 62, 4442-4448.
61. G. A. Cook, A. D. Kiffer, C. V. Klumpp, A. H. Mahk, L. A. Spence. Adv Chem. Ser. 1959, 21, 44-52.