Asymmetric aldol condensation as a route to polypropionate derived pheromones

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 3, 1996, Pages 423-428

  DiBattista, James P ^a   Webster, Francis X ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

aldol condensation; oxazolidinone; pheromone; sitophilate; sitophilure

Indexed keywords

PHEROMONE; SITOPHILATE; SITOPHILURE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029970496     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(96)00021-1     Document Type: Article

References (25)

1. (a) Heathcock, C.H. Science 1981, 214, 395;
2. (b) Evans, D.A.; Nelson, J.V.; Taber, T.R. Top. Stereochem. 1982, 13, 1;
3. (c) Mukaiyama, T. Organic Reactions; Wiley: New York, 1982; Vol. 28, p. 203;
4. (d) Heathcock, C.H. In Comprehensive Carbanion Chemistry, Burcel, E.; Durst, T. Eds.; Elsevier: Amsterdam, 1984; Part B, Ch. 4;
5. (e) Heathcock, C.H. In Asymmetric Synthesis; Morrison, J.D., Ed.; Academic Press: New York, 1984, Vol. 3, Ch. 2;
6. (f) Masamune, S.; Choy, W; Petersen, J.S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1;
7. (g) Braun, M. ibid. 1987, 26, 24.
8. Heathcock, C. H.; Buse, C. T., Kleschrick, W.A.; Perung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066.
9. Masamune, S.; Chow, W.; Kerdesky, F. A. J.; Imperiali, B. J. Am. Chem. Soc. 1981, 103, 1566.
10. Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503.
11. Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722.
12. Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1985, 26, 5807.
13. Evans, D. A. Ald. Acta, 1982, 75, 1.
14. Phillips, J. K.; Walgenbach, C. A.; Klein, J. A.; Burkholder, W. E.; Schmuff, N. R.; Fales, H. M. J. Chem. Real 1985, 11, 1263.
15. Chuman, T.; Mochizuki, K.; Mori, M.; Kohno, M.; Kato, K.; Noguchi, M. J. Chem. Ecol. 1985, 11, 417.
16. Evans, D. A.; Dow, R. L.; Shih, T. L.; Takas, J. M.; Zahler, R. J. Am. Chem. Soc. 1990, 772, 5290.
17. Evans, D. A.; Ennis, M. D.; Mather, D. J. J. Am. Chem. Soc. 1982, 104, 1737.
18. Mori, K.; Ishikura, M. Liebigs Ann. Chem. 1989, 1263.
19. Evans, D. A.; Miller, S. J.; Ennis, M. D.; Ornstein, P. L. J. Org. Chem. 1992, 57, 1067.
20. Corey, E. J.; Suggs, J. W. Tetrahedron Lett, 1975, 2647.
21. Mori, K.; Ebata, T. Tetrahedron 1986, 42, 4421.
22. Philips, J. K.; Miller, S. P. F.; Andersen, J. F.; Fales, H. M.; Burkholder, W. E. Tetrahedron Lett. 1987, 28, 6145.
23. Mochizoki, K.; Chuman, T.; Mori, M.; Kohno, M.; Kato, K. Agric. Biol. Chem. 1984, 48, 2833.
24. Kodama, H.; Ono, M.; Ohnishi, A. J. Chem. Ecol. 1987, 13, 1859.
25. Evans, D. A.; Rieger, D. C.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc., 1991, 113, 1047.