Studies Aimed at the Total Synthesis of Azadirachtin as an Insect Antifeedant

Journal of Toxicology - Toxin Reviews

Volumn 22, Issue 4, 2003, Pages 617-632

  Murai, Akio ^a,b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b NONE   (Japan)

Author keywords

Azadirachtin; Intramolecular Diels Alder reaction; Ireland Claisen rearrangement; Total synthesis

Indexed keywords

AZADIRACHTIN; DECALIN DERIVATIVE; DICHLORODIMETHYLSILANE; ESTER; FURAN DERIVATIVE; INSECT ANTIFEEDANT; INSECTICIDE; LIMONOID; LITHIUM DERIVATIVE; LITHIUM ENOLATE; SILANE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

AZADIRACHTA INDICA; CLAISEN REARRANGEMENT; CONFERENCE PAPER; DIELS ALDER REACTION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

ARACHNIDA; AZADIRACHTA INDICA; BETULACEAE; HEXAPODA; INSECTA;

EID: 0348014606     PISSN: 07313837     EISSN: None     Source Type: Journal    
DOI: 10.1081/TXR-120026917     Document Type: Conference Paper

References (39)

1. 5·Py·DMPU): A safer alternative to MoOPH for the α-hydroxylation of carbonyl compounds. Synlett. 107.
2. Bilton, J. N., Broughton, H. B., Jones, P. S., Ley, S. V., Lidert, Z., Morgan, E. D., Rzepa, H. S., Sheppard, R. N., Slawin, A. M. Z., Williams, D. J. (1987). X-ray crystallographic, mass spectroscopic, and NMR study of the limonoid insect antifeedant azadirachtin and related derivatives. Tetrahedron 43:2805.
3. Block, P. (1973). Bis(hydroxymethyl)malonate. Org. Synth., -Collect. Vol. 5:381.
4. Broughton, H. B., Ley, S. V., Slawin, A. M. Z., Williams, D. J., Morgan, E. D. (1986). X-ray crystallographic structure determination of detigloyldihydroazadirachtin and reassignment of the structure of the limonoid insect antifeedant azadirachtin. J. Chem. Soc., Chem. Commun. 46.
5. Brown, H. C., Jadhav, P. K. (1983). Asymmetric carbon-carbon bond formation via beta-allyldiisopinocampheylborane. simple synthesis of secondary homoallylic alcohols with excellent enantiomeric purities. J. Am. Chem. Soc. 105:2092.
6. Butterworth, J. H., Morgan, E. D. (1968). Isolation of a substance that suppressed feeding in locusts. Chem. Commun. 23.
7. Durand-Reville, T., Gobbi, L. B., Gray, B. L., Ley, S. V., Scott, J. S. (2002). Highly selective entry to the azadirachtin skeleton via a claisen rearrangement/radical cyclization sequence. Org. Lett. 4:3847.
8. Evans, D. A., Miller, S. J., Lectka, T. (1993a). Bis(oxazoline)copper(II) complexes as chiral catalysts for the enantioselective Diels-Alder reaction. J. Am. Chem. Soc. 115:6460.
9. Evans, D. A., Lectka, T., Miller, S. J. (1993b). Bis(imine)-copper(II) complexes as chiral Lewis acid catalysts for the Diels-Alder reaction. Tetrahedron Lett. 34:7027.
10. Fukuzaki, T., Kobayashi, S., Hibi, T., Ikuma, Y., Ishihara, J., Kanoh, N., Murai, A. (2002). Studies aimed at the total synthesis of azadirachtin. a modeled connection of C-8 and C-14 in azadirachtin. Org. Lett. 4:2877.
11. Govindachari, T. R., Gopalakrishnan, G. (1998). Supermolecules for insect control. J. Indian Chem. Soc. 75:655.
12. Henry, K. J. Jr., Fraser-Reid, B. (1994). Free radical methodology for carbohydrate to carbocycle transformations: An efficient synthesis of the tricyclic dihydrofuran portion of azadirachtin. J. Org. Chem. 59:5128.
13. Henry, K. J. Jr., Grieco, P. A., Jagoe, C. T. (1992). Chelation controlled addition of allylstannanes to aldehydes in lithium perchlorate-diethyl ether. Tetrahedron Lett. 33:1817.
14. Ho, G. -J., Methre, D. J. (1995). Lithium-initiated imide formation. A simple method for N-acylation of 2-oxazolidinones and bornane- 2,10-sultam. J. Org. Chem. 60:2271.
15. Ireland, R. E., Mueller, R. H. (1972). Claisen rearrangement of allyl esters. J. Am. Chem. Soc. 94:5897.
16. Ireland, R. E., Mueller, R. H., Willard, A. K. (1976). The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation. J. Am. Chem. Soc. 98:2868.
17. Ireland, R. E., Wipf, P., Armstrong, J. D. III. (1991). Stereochemical control in the ester enolate Claisen rearrangement. 1. Stereoselectivity in silyl ketene acetal formation. J. Org. Chem. 56:650.
18. Ishihara, J., Yamamoto, Y., Kanoh, N., Murai, A. (1999a). Synthetic studies on azadirachtin: construction of the highly functionalized decalin moiety of azadirachtin. Tetrahedron Lett. 40:4387.
19. Ishihara, J., Fukuzaki, T., Murai, A. (1999b). Synthetic studies on azadirachtin (part 3): Asymmetric synthesis of the tricyclic dihydrofuran moiety of azadirachtin. Tetrahedron Lett. 40:1907.
20. Kanoh, N., Ishihara, J., Murai, A. (1995). Construction of the tricyclic transdecalin framework of azadirachtins via intramolecular diels-Alder reaction. Synlett. 895.
21. Kanoh, N., Ishihara, J., Murai, A. (1997). Synthetic study on azadirachtin: asymmetric synthesis of the tetracyclic decalin part of azadirachtin. Synlett. 737.
22. Kanoh, N., Ishihara, J., Yamamoto, Y., Murai, A. (2000). Synthetic studies on azadirachtin: asymmetric synthesis of the tetracyclic decalin part of azadirachtin. Synthesis. 1878.
23. Kraus, W., Bokel, M., Klenk, A., Pohnl, H. (1985). The structure of azadirachtin and 22,23-dihydro-23-methoxyazadirachtin. Tetrahedron Lett. 26:6435.
24. Kraus, W., Bokel, M., Bruhn, A., Cramer, R., Klaiber, I., Klenk, A., Nagl, G., Pöhnl, H., Sadio, H., Vogler, B. (1987). Structure determination by nmr of azadirachtin and related compounds from azadirachta indica a. Juss (Meliaceae). Tetrahedron 43:2817.
25. Ley, S. V., Lovell, H., Williams, D. J. (1992). Chemistry of insect antifeedants from azadirachta indica, part 14: absolute configuration of azadirachtin. J. Chem. Soc., Chem. Commun. 1304.
26. Ley, S. V., Denholm, A. A., Wood, A. (1993). The chemistry of azadirachtin. Nat. Prod. Rep. 109, and references therein.
27. Ley, S. V., Gutteridge, C. E., Pape, A. R., Spilling, C. D., Zumbrunn, C. (1999). Chemistry of insect antifeedants from azadirachta indica (Part 22): functionalisation of the decalin fragment of azadirachtin via a claisen rearrangement reaction. Synlett. 1295.
28. Mitsunobu, O. (1981). The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis. 1.
29. Mordue (Luntz), A. J., Blackwell, A. (1993). Azadirachtin: an update. J. Insect Physiol. 39:903.
30. Nicolaou, K. C., Follmann, M., Roecker, A. J., Hunt, K. W. (2002a). Model studies towards azadirachtin: part 1. construction of the crowded C8C14 bond by radical chemistry. Angew. Chem., Int. Ed. 41:2103.
31. Nicolaou, K. C., Roecker, A. J., Follmann, M., Baati, R. (2002b). Model studies towards azadirachtin: part 2. construction of the crowded C8C14 bond by transition metal chemistry. Angew. Chem., Int. Ed. 41:2107.
32. Nishikimi, Y., Iimori, T., Sodeoka, M., Shibasaki, M. (1989). Synthetic studies of azadirachtin. Synthesis of the cyclic acetal intermediate in the naturally occurring form. J. Org. Chem. 54:3354.
33. Ohtani, I., Kusumi, T., Kashman, Y., Kakisawa, H. (1991). High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. J. Am. Chem. Soc. 113:4092.
34. Turner, C. J., Tempesta, M. S., Taylor, R. B., Zagorsky, M. G., Termini, J. S., Schroeder, D. R., Nakanishi, K. (1987). An NMR spectroscopic study of azadirachtin and its trimethyl ether. Tetrahedron 43:2789.
35. Wadsworth, W. S. Jr. (1977). Synthetic applications of phosphoryl-stablilized anions. Org. React. (New York) 25:73.
36. Watanabe, H., Watanabe, T., Mori, K. (1996). Enantioselective synthesis of the tricyclic furan moiety of azadirachtin, a potent insect antifeedant. Tetrahedron 52:13939.
37. Watanabe, H., Watanabe, T., Mori, K., Kitahara, T. (1997). Synthetic study on azadirachtin (part 2). Construction of the decalin moiety with full functionality on B-ring. Tetrahedron Lett. 37:4429.
38. Yamamoto, Y., Ishihara, J., Kanoh, N., Murai, A. (2000). Synthetic studies on azadirachtin: an efficient asymmetric synthesis of the highly functionalized tricyclic decalin part of azadirachtin. Synthesis. 1894.
39. Zanno, P. R., Miura, I., Nakanishi, K., Elder, D. L. (1975). Structure of the insect phagorepellent azadirachtin. Application of PRFT/CWD [partially relaxed Fourier transform/continuous wave decoupling] carbon-13 nuclear magnetic resonance. J. Am. Chem. Soc. 97:1975.