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

References

• Anderson J. C., Smith S. C. Oxodiperoxymolybdenum(pyridine)‐1,3‐dimethyl1‐3,4,5,6‐tetrahydro‐2(1H)‐pyrimidinone (MoO5·Py·DMPU): A safer alternative to MoOPH for the α‐hydroxylation of carbonyl compounds. Synlett 1990; 107
   Google Scholar
• 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. X‐ray crystallographic, mass spectroscopic, and NMR study of the limonoid insect antifeedant azadirachtic and related derivatives. Tetrahedron 1987; 43: 2805
   Google Scholar
• Block P. Bis(hydroxymethyl)malonate. Org. Synth., Collect. Vol. 1973; 5: 381
   Google Scholar
• Broughton H. B., Ley S. V., Slawin A. M.Z., Williams D. J., Morgan E. D. X‐ray crystallographic structure determination of detigloyldihydroazadirachtin and reassignment of the structure of the limonoid insect antifeedant azadirachtin. J. Chem. Soc., Chem. Commun. 1986; 46
   Google Scholar
• Brown H. C., Jadhav P. K. Asymmetric carbon‐carbon bond formation via beta‐allyldiisopinocampheylborane. simple synthesis of secondary homoallylic alcohols with excellent enantiometric purities. J. Am. Chem. Soc. 1983; 105: 2092
   Web of Science ®Google Scholar
• Butterworth J. H., Morgan E. D. Isolation of a substance that suppressed feeding in locusts. Chem. Commun 1968; 23
   Google Scholar
• Durand‐Reville T., Gobbi L. B., Gray B. L., Ley S. V., Scott J. S. Highly selective entry to the azadirachtin skeleton via a claisen rearrangement/radical cyclization sequence. Org. Lett. 2002; 4: 3847
   PubMed Web of Science ®Google Scholar
• Evans D. A., Miller S. J., Lectka T. Bis(oxazoline)copper(II) complexes as chiral catalysts for the enantioselective Diels‐Alder reaction. J. Am. Chem. Soc. 1993a; 115: 6460
   Web of Science ®Google Scholar
• Evans D. A., Lectka T., Miller S. J. Bis(imine)‐copper(II) complexes as chiral lewis acid catalysts for the Diels‐Alder reaction. Tetrahedron Lett. 1993b; 34: 7027
   Web of Science ®Google Scholar
• Fukuzaki T., Kobayashi S., Hibi T., Ikuma Y., Ishihara J., Kanoh N., Murai A. Studies aimed at the total synthesis of azadirachtin. a modeled connection of C‐8 and C‐14 in azadirachtin. Org. Lett. 2002; 4: 2877
   Google Scholar
• Govindachari T. R., Gopalakrishnan G. Supermolecules for insect control. J. Indian Chem. Soc. 1998; 75: 655
   Google Scholar
• Henry K. J., Jr., Fraser‐Reid B. Free radical methodology for carbohydrate to carbocycle transformations: An efficient synthesis of the tricyclic dihydrofuran portion of azadirachtin. J. Org. Chem. 1994; 59: 5128
   Google Scholar
• Henry K. J., Jr., Grieco P. A., Jagoe C. T. Chelation controlled addition of allylstannanes to aldehydes in lithium perchlorate‐diethyl ether. Tetrahedron Lett. 1992; 33: 1817
   Web of Science ®Google Scholar
• Ho G.‐J., Methre D. J. Lithium‐initiated imide formation. A simple method for N‐acylation of 2‐oxazolidinones and bornane‐2,10‐sultam. J. Org. Chem. 1995; 60: 2271
   Web of Science ®Google Scholar
• Ireland R. E., Mueller R. H. Claisen rearrangement of allyl esters. J. Am. Chem. Soc. 1972; 94: 5897
   Web of Science ®Google Scholar
• Ireland R. E., Mueller R. H., Willard A. K. The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation. J. Am. Chem. Soc. 1976; 98: 2868
   Web of Science ®Google Scholar
• Ireland R. E., Wipf P., Armstrong J. D., III. Stereochemical control in the ester enolate Claisen rearrangement. 1. Stereoselectivity in silyl ketene acetal formation. J. Org. Chem. 1991; 56: 650
   Google Scholar
• Ishihara J., Yamamoto Y., Kanoh N., Murai A. Synthetic studies on azadirachtin: construction of the highly functionalized decalin moiety of azadirachtin. Tetrahedron Lett. 1999a; 40: 4387
   Google Scholar
• Ishihara J., Fukuzaki T., Murai A. Synthetic studies on azadirachtin (part 3): Asymmetric synthesis of the tricyclic dihydrofuran moiety of azadirachtin. Tetrahedron Lett. 1999b; 40: 1907
   Google Scholar
• Kanoh N., Ishihara J., Murai A. Construction of the tricyclic trans‐decalin framework of azadirachtins via intramolecular diels‐Alder reaction. Synlett 1995; 895
   Google Scholar
• Kanoh N., Ishihara J., Murai A. Synthetic study on Azadirachtin: asymmetric synthesis of the tetracyclic decalin part of azadirachtin. Synlett 1997; 737
   Google Scholar
• Kanoh N., Ishihara J., Yamamoto Y., Murai A. Synthetic studies on azadirachtin: asymmetric synthesis of the tetracyclic decalin part of azadirachtin. Synthesis 2000; 1878
   Google Scholar
• Kraus W., Bokel M., Klenk A., Pohnl H. The structure of azadirachtin and 22,23‐dihydro‐23‐methoxyazadirachtin. Tetrahedron Lett. 1985; 26: 6435
   Google Scholar
• Kraus W., Bokel M., Bruhn A., Cramer R., Klaiber I., Klenk A., Nagl G., Pöhnl H., Sadio H., Vogler B. Structure determination by nmr of azadirachtin and related compounds from azadirachta indica a. Juss (Meliaceae). Tetrahedron 1987; 43: 2817
   Web of Science ®Google Scholar
• Ley S. V., Lovell H., Williams D. J. Chemistry of insect antifeedants from azadirachta indica, part 14: Absolute configuration of azadirachtin. J. Chem. Soc., Chem. Commun. 1992; 1304
   Google Scholar
• Ley S. V., Denholm A. A., Wood A. The chemistry of azadirachtin. Nat. Prod. Rep. 1993; 109, and references therein
   Google Scholar
• Ley S. V., Gutteridge C. E., Pape A. R., Spilling C. D., Zumbrunn C. Chemistry of insect antifeedants from azadirachta indica (Part 22): Functionalisation of the decalin fragment of azadirachtin via a claisen rearrangement reaction. Synlett 1999; 1295
   Google Scholar
• Mitsunobu O. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis 1981; 1
   Web of Science ®Google Scholar
• Mordue (Luntz) A. J., Blackwell A. Azadirachtin: an update. J. Insect Physiol. 1993; 39: 903
   Web of Science ®Google Scholar
• Nicolaou K. C., Follmann M., Roecker A. J., Hunt K. W. Model studies towards azadirachtin: part 1. construction of the crowded C8C14 bond by radical chemistry. Angew. Chem., Int. Ed. 2002a; 41: 2103
   Google Scholar
• Nicolaou K. C., Roecker A. J., Follmann M., Baati R. Model studies towards azadirachtin: part 2. construction of the crowded C8C14 bond by transition metal chemistry. Angew. Chem., Int. Ed. 2002b; 41: 2107
   Google Scholar
• Nishikimi Y., Iimori T., Sodeoka M., Shibasaki M. Synthetic studies of azadirachtin. Synthesis of the cyclic acetal intermediate in the naturally occurring form. J. Org. Chem. 1989; 54: 3354
   Web of Science ®Google Scholar
• Ohtani I., Kusumi T., Kashman Y., Kakisawa H. High‐field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. J. Am. Chem. Soc. 1991; 113: 4092
   Web of Science ®Google Scholar
• Turner C. J., Tempesta M. S., Taylor R. B., Zagorsky M. G., Termini J. S., Schroeder D. R., Nakanishi K. An NMR spectroscopic study of azadirachtin and its trimethyl ether. Tetrahedron 1987; 43: 2789
   Google Scholar
• Wadsworth W. S., Jr. Synthetic applications of phosphoryl‐stablilized anions. Org. React. (New York) 1977; 25: 73
   Web of Science ®Google Scholar
• Watanabe H., Watanabe T., Mori K. Enantioselective synthesis of the tricyclic furan moiety of azadirachtin, a potent insect antifeedant. Tetrahedron 1996; 52: 13939
   Google Scholar
• Watanabe H., Watanabe T., Mori K., Kitahara T. Synthetic study on azadirachtin (part 2). Construction of the decalin moiety with full functionality on B‐ring. Tetrahedron Lett. 1997; 37: 4429
   Google Scholar
• Yamamoto Y., Ishihara J., Kanoh N., Murai A. Synthetic studies on azadirachtin: an efficient asymmetric synthesis of the highly functionalized tricyclic decalin part of azadirachtin. Synthesis 2000; 1894
   Google Scholar
• Zanno P. R., Miura I., Nakanishi K., Elder D. L. 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. 1975; 97: 1975
   PubMed Web of Science ®Google Scholar