Spinosyn G: Proof of structure by semisynthesis

Journal of Organic Chemistry

Volumn 70, Issue 6, 2005, Pages 2154-2160

  Graupner, Paul R ^a   Martynow, Jacek ^a,b   Anzeveno, Peter B ^a,c  

^a DOW AGROSCIENCES LLC   (United States)

^b INDUSTRIAL CHEMISTRY RESEARCH INSTITUTE   (Poland)

^c ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINATION; FERMENTATION; NITROGEN; OXIDATION; REACTION KINETICS; REDUCTION; STEREOCHEMISTRY; SUGARS; SYNTHESIS (CHEMICAL);

GLYCOSIDE; NATURAL PRODUCTS; SEMISYNTHESIS; SPINOSYN G;

INSECTICIDES;

4 (N METHYL N TRICHLOROETHOXYCARBONYLAMINO) 1,2,3,4,6 PENTADEOXY THREO HEXENOPYRANOSE; 4'' EPISPINOSYN A; 4'' KETONE; 5'' EPISPINOSYN A; ALCOHOL; AZIDE; DESDIMETHYLAMINO 4'' AZIDOSPINOSYN A; GLYCOSIDE; KETONE DERIVATIVE; MACROCYCLIC COMPOUND; METHYL GROUP; METHYL OSSAMINIDE; N NOR N TRICHLOROETHOXYCARBONYLOSSAMINYLSPINOSYN A 17 PSEUDOAGLYCONE; NATURAL PRODUCT; NITROGEN; PYRAN DERIVATIVE; SPINOSYN A; SPINOSYN A 17 PSEUDOAGLYCONE; SPINOSYN G; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DEAMINATION; DEPROTECTION REACTION; METHYLATION; OXIDATION; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

GLYCOSIDES; INSECTICIDES; MACROLIDES; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 15444366583     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048173k     Document Type: Article

References (22)

1. (a) Omura, S.; Nakagawa, A.; Otani, M.; Haa, T. J. Am. Chem. Soc. 1969, 91, 3401.
2. (b) Omura, S.; Sadakane, N.; Tanaka, Y.; Matsubara, H. J. Antibiot. 1983, 36, 927.
3. (c) Sun, C.; Wei, J.; Huang, J.; Jin, W.; Wang, Y. Actinomycetologica 1999, 13, 120.
4. (a) Boeck, L. D.; Chio, E. H.; Eatin, T. E.; Godfrey, O. W.; Michel, K. H.; Nakatsukasa, W. M.; Yao, R. C. (Eli Lilly) Eur. Pat. Appl. EP 375 316, 1990; Chem. Abstr. 1991, 114, 80066.
5. (b) Kirst, H. A.; Michel, K. H.; Mynderse, J. S.; Chio, E. E.; Yao, R. C.; Nakatsukasa, W. M.; Boeck, L. D.; Occolowitz, J. L.; Paschal, J. W.; Deeter, J. B.; Thompson, G. D. In Synthesis and Chemistry of Agrochemicals III; Baker, D. R., Fenyes, J. G., Steffens, J. J., Eds.; ACS Symposium Series 504; The American Chemical Society, Washington, DC, 1992; pp 216-225.
6. (a) Stevens, C. L.; Gutowski, G. E.; Byant, C. P.; Glinski, R. P.; Edwards, O. E.; Sharma, G. M. Tetrahedron Lett. 1969, 10, 1181.
7. (b) Kirst, H. A.; Mynderse, J. S.; Martin, J. W.; Baker, P. J.; Paschal, J. W.; Rios Steiner, J. L.; Lobkovsky, E.; Clardy, J. J. Antibiot. 1996, 49, 162.
8. Hochlowski, J. E.; Mullally, M. M.; Brill, G. M.; Whittern, D. N.; Buko, A. M.; Hill, P.; McAlpine, J. B. J. Antibiot. 1991, 44, 1318.
9. (a) Albini, A. Synthesis 1993, 263.
10. (b) Michelot, R. Bull. Soc. Chim. Fr. 1969, 4377.
11. (a) Murahashi, S.-I. Angew. Chem., Int. Ed. Engl. 1995, 34, 2443.
12. (b) Goti, A.; Romani, M. Tetrahedron Lett. 1994, 35, 6567.
13. (c) Murahashi, S.-I.; Naota, T.; Miyaguchi, N.; Nakato, T. Tetrahedron Lett. 1992, 33, 6991.
14. (d) Rousselet, G.; Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1995, 36, 4999.
15. Bax, A.; Davis, D. G. J. Magn. Reson. 1985, 63, 207.
16. (a) DeAmicis, C. V.; Anzeveno, P. B.; Martynow, J. G.; McLaren, K. L.; Green, F. R., III; Sparks, T. C.; Kirst, H. A.; Creemer, L. C.; Worden, T. V.; Schoonover, J. R.; Gifford, J. M.; Hatton, C. J.; Hegde, V. B.; Crouse, G. D.; Thoreen, B. R.; Ricks, M. J. U.S. Patent 6,001,981, 1999; Chem. Abstr. 1999, 132, 35986.
17. (b) Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1993, 115, 4497.
18. (c) Paquette, L. A.; Collado, I.; Purdie, M. J. Am. Chem. Soc. 1998, 120, 2553.
19. (a) Brimacombe, J. S.; Douer, L. W.; Rollins, A. J. J. Chem. Soc., Perkin Trans, 1 1972, 2977.
20. (b) Malik, A.; Afza, N.; Voelter, W. Ann. 1984, 636.
21. (c) Malik, A.; Afza, N.; Voelter, W. J. Chem. Soc., Perkin Trans. 1 1983, 2103.
22. Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis; John Wiley and Sons: New York, 1968; Vol. 1, p 1276.