Stereoselective Synthesis of Alkyl (2E, 4E)- and (2Z, 4E)-3,7,11-Trimethyl-2,4-dodecadienoates. Insect Growth Regulators with Juvenile Hormone Activity

Journal of Organic Chemistry

Volumn 40, Issue 1, 1975, Pages 1-7

  Henrick, Clive A ^a   Willy, W Edward ^a   Baum, John W ^a   Baer, Ted A ^a   Garcia, Barbara A ^a   Mastre, Thomas A ^a   Chang, Samuel M ^a  

^a Zoecon Research and Development   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,7,11 TRIMETHYLDODECA 2,4 DIENOIC ACID DERIVATIVE; DRUG ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROMETRY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THEORETICAL STUDY; ALKYLATION; ANIMAL; ARTICLE; METHYLATION; STEREOISOMERISM; SYNTHESIS;

JUVENILE HORMONE; UNSATURATED FATTY ACID;

ALKYLATION; ANIMAL; FATTY ACIDS, UNSATURATED; JUVENILE HORMONES; METHYLATION; STEREOISOMERISM;

EID: 0016847303     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00889a001     Document Type: Article

References (51)

1. C. A. Henrick, G. B. Staal, and J. B. Siddall, J. Agr. Food Chem., 21, 354(1973).
2. S. G. Nassar, G. B. Staal, and N. I. Armanious, J. Econ. Ent., 66, 847 (1973).
3. G. B. Staal, S. Nassar, and J. W. Martin, J. Econ. Ent., 66, 851 (1973).
4. C. A. Henrick and J. B. Siddall, Belgian Patent 778,242 (Jan 19, 1972).
5. C. A. Henrick, Belgian Patent 778,241 (Jan 19, 1972).
6. C. A. Henrick, U. S. Patent 3,773,793 (Nov 20, 1973).
7. C. A. Henrick, German Patent 2,332,601 (Feb 28, 1974).
8. C. A. Henrick, U. S. Patent 3,818,047 (June 18, 1974).
9. C. A. Henrick, W. E. Willy, B. A. Garcia, and G. B. Staal, J. Agr. Food Chem., submitted for publication.
10. W. Stilz and H. Pommer, U. S. Patents 3,163,669 (Dec 29, 1964).
11. W. Stilz and H. Pommer, U. S. Patents 3,177,226 (April 6, 1965).
12. C. A. Henrick, W. E. Willy, D. R. McKean, E. Baggiolini, and J. B. Siddall, J. Org. Chem., 40, 8 (1975).
13. F. Feist and O. Beyer, Justus Liebigs Ann. Chem., 345, 117 (1906).
14. C. D. Hurd and J. L. Abernethy, J. Amer. Chem. Soc., 63, 976 (1941).
15. V. Petrow and O. Stephenson, J. Chem. Soc., 1310(1950).
16. C. D. Robeson, J. D. Cawley, L. Weisler, M. H. Stern, C. C. Eddinger, and A. J. Chechak, J. Amer. Chem. Soc., 77, 4111 (1955).
17. J. D. Cawley, J. Amer. Chem. Soc., 77, 4125 (1955).
18. J. D. Cawley and D. R. Nelan, J. Amer. Chem. Soc., 77, 4130 (1955).
19. C. D. Robeson and J. D. Cawley, British Patent 701,807 (Jan 6, 1954).
20. C. D. Robeson and J. D. Cawley, U. S. Patents 2,709,711 and 2,709,712 (May 31, 1955).
21. R. H. Wiley and H. G. Ellert, J. Amer. Chem. Soc., 79, 2266 (1957).
22. R. H. Wiley, J. Chem. Soc., 3831 (1958).
23. R. H. Wiley, E. Imoto, R. P. Houghton, and P. Veeravagu, J. Amer. Chem. Soc., 82, 1413 (1960).
24. R. H. Wiley, P. F. G. Nau, and T. H. Crawford, J. Org. Chem., 26, 4285 (1961).
25. R. H. Wiley, P. F. G. Nau, H. C. van der Pias, and T. H. Crawford, J. Org. Chem., 27, 1991 (1962).
26. D. S. Young and G. F. Rodgers, U. S. Patent 2,673,212 (March 23, 1954).
27. D. S. Young and G. F. Rodgers, Chem. Abstr., 49, 4710d(1955).
28. F. R. Goss, C. K. Ingold, and J. F. Thorpe, J. Chem. Soc., 123, 327 (1923).
29. R. H. Wiley and N. R. Smith, J. Amer. Chem. Soc., 73, 3531 (1951).
30. U. Eisner, J. A. Elvidge, and R. P. Unstead, J. Chem. Soc., 1372 (1953).
31. K. Eiter and E. Truscheit, German Patents 1,070,175 (Dec 3, 1959).
32. K. Eiter and E. Truscheit, German Patents I. 075,598 (Feb 18, 1960).
33. K. Eiter, E. Truscheit, and H. Oediger, Angew. Chem., 72, 948 (1960).
34. D. S. Sgoutas and F. A. Kummerow, Lipids, 4, 283 (1969).
35. U. T. Bhalerao and H. Rapoport, J. Amer. Chem. Soc., 93, 4835 (1971).
36. J. A. Klun, O. L. Chapman, K. C. Mattes, P. W. Wojtkowski, M. Beroza, and P. E. Sonnet, Science, 181, 661 (1973).
37. C. Moussebois and J. Dale, J. Chem. Soc. C, 260 (1966).
38. R. H. Pallen and C. Sivertz, Can. J. Chem., 35, 723 (1957).
39. I. A. Kopeva, E. I. Tinyakova, B. A. Dolgoplosk, L. I. Red'kina, and E. N. Zavadovskaya, Vysokomol. Soedin., Ser. A., 9, 645 (1967).
40. I. A. Kopeva, E. I. Tinyakova, B. A. Dolgoplosk, L. I. Red'kina, and E. N. Zavadovskaya, Chem. Abstr., 67, 33124e (1967).
41. E. J. Corey and E. Hamanaka, J. Amer. Chem. Soc., 89, 2758 (1967).
42. K. Gollnick and G. Schade, Tetrahedron Lett., 689 (1968).
43. J. I. Cunneen, G. M. C. Higgins, and W. F. Watson, J. Polym. Sci., 40, 1 (1959).
44. M. A. Golub in “The Chemistry of Alkenes,” Vol. 2, J. Zabicky, Ed., Interscience, New York, N.Y., 1970, Chapter 9, pp 449-460.
45. C. Walling and W. Helmreich, J. Amer. Chem. Soc., 81, 1144 (1959).
46. U. R. Nayak, A. H. Kapadi, and S. Dev, Tetrahedron, 26, 5071, 5083 (1970).
47. L. H. Hornig, H. Neu, and O. Probst, U. S. Patent 3,642,885 (Feb 15, 1972).
48. M. A. Golub in “The Chemistry of Alkenes,” Vol. 2, J. Zabicky, Ed., Interscience, New York, N.Y., 1970, Chapter 9, pp 468-474.
49. E. H. White and H. Scherrer, Tetrahedron Lett., 758 (1961).
50. E. H. White, A. A. Baum, and D. E. Eitel, Org. Syn., 48, 102 (1968).
51. W. L. Roelofs, A. Comeau, and R. Selle, Nature (London), 224, 723 (1969).