Bis-esters from maleic anhydrides under neutral conditions: Protection of the anhydride of the natural product cornexistin

Tetrahedron Letters

Volumn 37, Issue 12, 1996, Pages 1967-1970

  Fields, Stephen C ^a   Dent III, William H ^a   Green III, F Richard ^a   Tromiczak, Eric G ^a  

^a DOW AGROSCIENCES LLC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HERBICIDE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029881192     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00182-7     Document Type: Article

References (13)

1. Nakajima, M.; Itoi, K.; Takamatsu, Y.; Sato, S.; Furukawa, Y.; Furuya, K.; Honma, T.; Kadotani, J.; Kozasa, M.; Haneishi, T. J. Antibiotics 1991, 44, 1065.
2. Eisner, U.; Elvidge, J. A.; Linstead, R. P. J. Chem. Soc. 1951, 1501. Makowka, B. and Block, H. D. (Bayer Ag). United States Patent US 4,827,022; Date: 2 May 1989. CA: 88:287115141.
3. Eisner, U.; Elvidge, J. A.; Linstead, R. P. J. Chem. Soc. 1951, 1501. Makowka, B. and Block, H. D. (Bayer Ag). United States Patent US 4,827,022; Date: 2 May 1989. CA: 88:287115141.
4. Write to the major author of this publication for a reprint of the poster entitled "Four Decomposition Products from the Natural Product Cornexistin", L. Bjelk, W. H. Dent III, R. J. Eilers, S. C. Fields, E. G. Tromiczak, S. S. Thornburgh, given at the CU-Hauser Symposium, May 26, 1995, Boulder, Colorado.
5. 3, ppm) 9.38 (s, 1H) 6.81 (q, 1 H, J = 8.7 Hz) 4.81 (d, 1 H, J = 7.2 Hz) 3.96 (m, 1 H) 3.74 (s, 3 H) 3.39 (d, 1 H, J = 14 Hz) 3.29 (d, 1 H, J = 14 Hz) 2.38 (s, 3 H) 2.02 (d, 1 H, J = 7.2 Hz) 1.65-1.20 (m, 4 H) 0.91 (t, 3 H, J = 7.0 Hz). 13C NMR (1H decoupled, CDCl3, ppm) 193.4, 167.7, 167.2, 152.5, 140.1, 138.4, 130.6, 83.4, 77.3, 52.6, 41.9, 41.4, 28.4, 27.3, 19.9, 15.1, 14.2.
6. For example: Zilkha, A. and Bachi, M. D. J. Org. Chem. 1959, 24, 1096.
7. 3OD, ppm) 5.85 (q, 0.6 H, J = 7.0 Hz) 5.70 (q, 0.2 H, J = 7.0 Hz) 5.52 (q, 0.2 H, J = 7.0 Hz) 5.02-4.92 (dd, 0.2 H, J = 5.0 Hz, 9.9 Hz) 4.90-4.80 (dd, 0.8 H, J = 5.2 Hz, 9.2 Hz) 4.07 (d, 0.2 H, J = 10.2 Hz) 3.99 (d, 0.2 H, J = 10.3 Hz) 3.76 (d, J = 0.6 H, J = 9.6 Hz) 1.75 (d, 2.4 H, J = 7.0 Hz) 1.70 (d, 0.3 H, J = 7.0 Hz) 1.69 (d, 0.3 H, J = 7.0 Hz). The structures of 4a and 4b were confirmed by characterization of their sodium salts.
8. For example: Oren, J.; Demuth, M.; Fuchs, B. Synthesis 1987, 850.
9. Hashimoto, N.; Aoyama, T.; Shioiri, T. Chem. Pharm. Bull. 1981, 29, 1475.
10. 3, ppm) 218.1, 168.2, 140.9, 136.0, 134.8, 131.9, 77.3, 76.3, 67.8, 52.3, 45.4, 42.7, 42.6, 34.9, 30.6, 20.8, 14.0, 13.7.
11. 3, ppm) 7.35-7.25 (m, 5 H) 5.53 (q, 6 H, J = 7.0 Hz) 5.40 (d, 0.4 H, J = 7.0 Hz) 5.25-5.00 (m, 3 H) 4.80-4.72 (br m, 0.6H) 4.72-4.65 (br m, 0.4 H) 4.50-4.40 (br m, 1 H) 3.53 (s, 1.2 H) 4.24 (s, 1.8 H) 3.30-3.05 (br m, 3 H) 3.05-2.90 (br m, 1 H) 2.85-2.55 (br m, 2 H) 2.00-1.85 (br m, 1 H) 1.62 (d, 1.8 H, J = 7.0 Hz) 1.48 (d, 1.2 H, J = 7.0 Hz) 1.40-1.15 (m, 2 H) 1.15-0.95 (br m, 1 H) 0.79 (t, 1.8 H, J = 7.3 Hz) 0.71 (d, 1.2 H, J = 7.3 Hz).
12. Anantharamaiah, G. M. and Sivanandaiah, K. M. J. Chem. Soc., Perkin Trans. I 1977, 490.
13. 1H NMR.