Total Synthesis of Lavendamycin Methyl Ester

Journal of Organic Chemistry

Volumn 50, Issue 26, 1985, Pages 5790-5795

  Boger, Dale L ^a   Duff, Steven R ^a   Panek, James S ^a   Yasuda, Masami ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000112605     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00350a070     Document Type: Article

References (17)

1. Doyle, T. W.; Balitz, D. M.; Grulich, R. E.; Nettleton, D. E.; Gould, S. J.; Tann, C.-H.; Meows, A. E. Tetrahedron Lett, 1981, 22, 4595. For a recent review, see: Gould, S. J.; Weinreb, S. M. Fortschr. Chem. Org. Natur. 1982, 41, 77.
2. Balitz, D. M.; Bush, J. A.; Bradner, W. T.; Doyle, T. W.; O’Herron, F. A.; Nettleton, D. E. J. Antibiot. 1982, 35, 259.
3. Gould, S. J.; Cane, D. E. J. Am. Chem. Soc. 1982, 104, 343. Erickson, W. R.; Gould, S. J. J. Am. Chem. Soc. 1985, 107, 5831.
4. For the total synthesis of lavendamycin methyl ester and comparison with that derived from natural material, see: (a) Kende, A. S.; Ebetino, F. H. Tetrahedron Lett. 1984, 25, 923. Kende, A. S.; Ebetino, F. H.; Battista, R.; Lorah, D. P.; Lodge, E. Heterocycles 1984, 21, 91. Hibino, S.; Okazaki, M.; Ichikawa, M.; Sato, K.; Ishizu, T. Heterocycles 1985,23, 261. For the preparation of desmethyllavendamycin and related studies, see: (b) Hibino, S.; Okazaki, M.; Sato, K.; Morita, I. Heterocycles 1983, 20, 1957. (c) Rao, A. V. R.; Chavan, S.; Sivadasan, L. Indian J. Chem. Sect. B 1984, 23B, 496.
5. Boger, D. L.; Panek, J. S. Tetrahedron Lett. 1984, 25, 3175. (7) Boger, D. L.; Duff, S. R.; Panek, J. S.; Yasuda, M. J. Org. Chem., preceding paper in this issue.
6. (a) Weinreb, S. M.; Basha, F. Z.; Hibino, S.; Khatri, N. A.; Kim, D.; Pye, W. E. J. Am. Chem. Soc. 1982, 104, 536. Basha, F. Z.; Hibino, S.; Kim, D.; Pye, W. E.; Wu, T.-T.; Weinreb, S. M. J. Am. Chem. Soc. 1980, 102, 3962. (b) Kende, A. S.; Lorah, D. P.; Boatman, J. J. Am. Chem. Soc. 1981, 103, 1271. (c) Boger, D. L.; Panek, J. S. J. Org. Chem. 1983, 48, 621. Boger, D. L.; Panek, J. S. J. Am. Chem. Soc. 1985, 107, 5745. (d) Martin, J. C.J. Org. Chem. 1982, 47, 3761.
7. 4, Redal-H, and MeMgBr.
8. Compound iii was formed in variable yields as detailed (6–24 h). These and additional studies are provided as supplementary material.
9. Details of related efforts are provided as supplementary material. (12) A related effort to prepare and utilize the oxazinone ii was unsuccessful. Details of this and related efforts to selectively direct attack to the C-2 carboxylate of 3 are detailed in supplementary material.
10. Corey, E. J.; Chaykovsky, M. J. J. Am. Chem. Soc. 1965, 87, 1345. Meyers, A. I.; Durandetta, J. L.; Marava, R. J. Org. Chem. 1975, 40, 2025.
11. Studies on simple, related oxazinones which provided comparable findings are detailed in supplementary material.
12. 2) of the crude product provided 10 (54%). (16) Cheng, C. C.; Yan, S. J. Org. React. (N.Y.) 1982, 28, 37.
13. Deprotection at 25 °C or for longer periods of reaction time leads to a diminished yield of product.
14. 4, 1–18 h) were unsuccessful.
15. 1H NMR (300 MHz) of authentic material with that of 16 (300 MHz) confirmed that the materials are identical.
16. 2O, pentane, and hexane) were distilled before use. All reactions requiring anhydrous or inert conditions were run under a positive pressure of argon, and reagent was introduced by syringe through a septum. Syringes and reaction flasks were oven dried.
17. (a) Meyers, A. I.; Slack, J.; Smith, R. K.; Mihelich, E. D.; Hershenson, F. M.; Liang, C. D. J. Org. Chem. 1979, 44, 2277. (b) Stahl, E.; Mueller, J. Chromatographia 1982, 15, 493.