Carbohydrate based IMDA/aldol strategy towards the densely functionalized trans-decalin subunit of azadirachtin

Chemical Communications

Volumn , Issue 23, 1998, Pages 2577-2578

  Haag, Dieter ^a   Chen, Xiao Tao ^a   Fraser Reid, Bert ^a  

^a Nat Prod Glycotechnology Res I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AZADIRACHTIN; CARBOHYDRATE; DECALIN; GLYCOPYRANOSIDE; TERPENE;

ARTICLE; CHEMICAL STRUCTURE; DIASTEREOISOMER; SYNTHESIS;

EID: 0032494985     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a806400h     Document Type: Article

References (16)

1. B. Fraser-Reid and R. C. Anderson, Prog. Chem. Org. Nat. Prod., 1980, 39, 1;
2. B. Fraser-Reid and R. Tsang, in Strategies and Tactics in Organic Synthesis, ed T. Lindberg, Academic Press, New York, 1989, vol. 2, pp 123-162.
3. J. C. López and B. Fraser-Reid, Chem. Commun., 1997, 2251.
4. R. Tsang and B. Fraser-Reid, J. Org. Chem., 1992, 57, 1065.
5. J. C. López, A. M. Gómez and B. Fraser-Reid, J. Chem. Soc., Chem. Commun., 1993, 762.
6. I. R. Hanson, Nat. Prod. Rep., 1998, 15, 93.
7. S. V. Ley, A. A. Denholm and A. Wood, Nat. Prod. Rep., 1993, 10, 109.
8. M. Jacobson, Pharmacology and Toxicity of Neem, in Focus on Phytochemical Pesticides, The Neem Tree, ed. J. Jacobson, CRC Press, 1989; vol. 1, p 133.
9. For some examples of synthetic approaches to the azadirachtins, see: S. V. Ley, Pure Appl. Chem., 1994, 66, 2099;
10. H. Watanabe, T. Watanabe, K. Mori and T. Kitahara, Tetrahedron Lett., 1997, 38, 4429;
11. N. Konah, J. Ishihara and A. Murai, Synlett, 1997, 737.
12. S. J. Danishefsky and J. F. Kerwin Jr., J. Org. Chem., 1982, 47, 3805.
13. R. J. Ferrier and S. Middleton, Chem. Rev., 1993, 93, 2779.
14. R. Pappo, D. S. Allen Jr., R. U. Lemieux and W. S. Johnson, J. Org. Chem., 1956, 21, 478.
15. D. A. Evans, J. V. Nelson, E. Vogel and T. R. Taber, J. Am. Chem. Soc., 1981, 103, 3099.
16. D. F. Taber, Intramolecular Diels-Alder and Alder Ene Reactions, Springer-Verlag, 1984.