Enantioselective synthesis of the tricyclic furan moeity of azadirachtin, a potent insect antifeedant

Tetrahedron

Volumn 52, Issue 44, 1996, Pages 13939-13950

  Watanabe, Hidenori ^a   Watanabe, Takeru ^a   Mori, Kenji ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZADIRACHTIN;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

INSECTA;

EID: 0030605153     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00856-3     Document Type: Article

References (27)

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20. 8. See ref. 5c and refs. cited therein.
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24. 12. Due to the steric hindrance of the lactone carbonyl, the first reduction of 8b to generate A was thought to be slower than the undesired further reactions (A→B→C). TMSCl is supposed to promote the first step as a Lewis acid and/or capture the alkoxide of A to avoid lactol-ring opening. (equation presented)
25. 13. See refs. 1b and refs. cited therein.
26. 14. Ley et al. reported 13 and 14 to have shown almost the same and a half anifeedant activity of azadirachtin against Spodoptera littoralis (Boisduval), respectively. See ref. 1a and refs. cited therein.
27. 15. For the assay procedure see: Allan, E. J.; Eeswara, J. P.; Johnson, S; Mordue, A.J.; Morgan, E. D.; Stuchbury, T. Pestic. Sci. 1994, 42, 147-152.