Total Synthesis of (+)-18-Deoxynargenicin A1

Journal of the American Chemical Society

Volumn 110, Issue 12, 1988, Pages 4041-4042

  Plata, Daniel J ^a   Kallmerten, James ^a  

^a SYRACUSE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

18 DEOXYNARGENICIN A1; UNCLASSIFIED DRUG;

DRUG SYNTHESIS; NONHUMAN; PRELIMINARY COMMUNICATION;

EID: 0023950935     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00220a055     Document Type: Article

References (24)

1. Celmer, W. D.; Chmurny, G. N.; Moppett, C. E.; Ware, R. S.; Watts, P. C.; Whipple, E. B. J. Am. Chem. Soc. 1980, 102, 4203.
2. Whaley, H. A.; Chidester, C. G.; Miszak, S. A.; Wnuk, R. J. Tetrahedron Lett. 1980, 21, 3659.
3. The absolute configuration shown for nargenicin A, has been proposed on the basis of an observed positive Cotton effect in the CD spectrum of the O-l 1-nitrobenzyl ester of 1: Cane, D. E.; Yang, C.-C. J. Antibiot. 1985, 38, 423.
4. Whaley, H. A.; Coates, J. H., Abstract No. 187 from the 21st Interscience Conference of Antimicrobial Agents and Chemotherapy, November 4, 1981. The structure of 18-deoxynargenicin has been confirmed by synthetic conversion of 1 to 3: Magerlein, B. J.; Reid, R. J. J. Antibiot. 1982, 35, 254.
5. Tone, J.; Shibakawa, R.; Maeda, H.; Yamauchi, Y.; Niki, K.; Saito, M.; Tsukuda, K.; Whipple, E. B.; Watts, P. C.; Moppett, C. E.; Jefferson, M. T.; Huang, L. H.; Cullen, W. P.; Celmer, W. D. Abstract No. 62 from the 20th Interscience Conference of Antimicrobial Agents and Chemotherapy, September 22, 1980.
6. Celmer, W. D.; Cullen, W. P.; Shibakawa, R.; Tone, J. (to Pfizer Inc., New York) U.S. Patent 4, 435, 747. See Chem. Abstr. 1984, 101, 53332.
7. The structure of coloradocin, a bis-macrolide related to the nargenicins, has been reported: Rasmussen, R. R.; Scherr, M. H.; Whittern, D. N.; Buko, B. N.; McAlpine, J. B. J. Antibiot. 1987, 40, 1383.
8. Magerlein, B. J.; Miszak, S. A. J. Antibiot. 1982, 35, 111.
9. Magerlein, B. J. Abstract No. Medi 72 from the 182nd National Meeting of the American Chemical Society, August 23–28, 1981.
10. Cane, D. E.; Yang, C.-C. J. Am. Chem. Soc. 1984, 106, 784.
11. Snyder, W. C.; Rinehart, K. L. J. Am. Chem. Soc. 1984, 106, 787.
12. Kallmerten, J. Tetrahedron Lett. 1984, 25, 2843.
13. Kallmerten, J.; Plata, D. J. Heterocycles 1987, 25, 145.
14. Jones, R. C. F.; Tunnicliffe, J. H. Tetrahedron Lett. 1985, 26, 5845.
15. Roush, W. R.; Coe, J. W. Tetrahedron Lett. 1987, 28, 931.
16. Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130.
17. Corey, E. J.; Trybulski, E. J.; Melvin, L. S.; Nicolaou, K. C.; Secrist, J. A.; Lett, R.; Sheldrake, P. W.; Falck, J. R.; Brunelle, D. J.; Haslanger, M. F.; Kim, S.; Yoo, S. J. Am. Chem. Soc. 1978, 100, 4618.
18. 1H NMR analysis of the corresponding Mosher ester.
19. Salmond, W. G.; Barta, M. A.; Havens, J. L. J. Org. Chem. 1978, 43, 2057.
20. Ireland, R. E.; Muchmore, D. C.; Hentgartner, U. J. Am. Chem. Soc. 1972, 94, 5098.
21. Ireland, R. E.; Pfister, G. Tetrahedron Lett. 1969, 2145.
22. Vedejs, E. J. Am. Chem. Soc. 1974, 96, 5944.
23. Vedejs, E.; Telschow, J. E. J. Ore. Chem. 1976, 41, 740.
24. Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614.