Synthesis of the tricyclic dihydrofuran moiety of azadirachtin: Efficient transformation of the Claisen rearrangement intermediate into a functionalized tricyclic dihydrofuran core

Tetrahedron

Volumn 59, Issue 51, 2003, Pages 10287-10294

  Ishihara, Jun ^a   Ikuma, Yohei ^b   Hatakeyama, Susumi ^a   Suzuki, Takanori ^b   Murai, Akio ^b  

^a NAGASAKI UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Azadirachtin; Claisen rearrangement; Deoxygenation

Indexed keywords

7 HYDROXY 9 METHYL 11 (1 METHYLCYCLOHEXYL) 2,4,10 TRIOXATETRACYCLO[6.3.1.0 3,7 .0 9,11 ]DODEC 5 ENE; AZADIRACHTIN; ESTER DERIVATIVE; FURAN DERIVATIVE; LIMONOID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CLAISEN REARRANGEMENT; PRIORITY JOURNAL; SYNTHESIS; THEORETICAL MODEL;

AZADIRACHTA INDICA; HEXAPODA;

EID: 0345357983     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.10.062     Document Type: Article

References (69)

1. (a) Murai A. Greenhalgh R., Roberts T.R. Pesticide Science and Biotechnology. 1987;81-88 Blackwell, London
2. (b) Neem: A Tree for solving Global Problems. 1992;National Research Council, National Academy, Washington, DC
3. (c) Gill J.S., Lewis C.T. Nature. 232:1971;402
4. (d) Ruscoe C.N.E. Nature. 236:1972;159
5. (e) Rembold H., Garcia D.W.E. J. Insect. Physiol. 30:1984;939
6. (f) Redfern R.E., Hayes D.K., Warthen J.D., DeMilo A.B., McGovern T.P. Ann. Rev. Chronopharmacol. 1:1984;239
7. (g) Koul O. Entomol. Exp. Appl. 36:1984;85
8. (h) Mordue (Luntz) A.J., Blackwell A. J. Insect Physiol. 39:1993;903
9. (i) Govindachari T.R., Gopalakrishnan G. J. Indian Chem. Soc. 75:1998;655.
10. (a) Butterworth J.H., Morgan E.D. Chem. Commun. 1968;23
11. (b) Butterworth J.H., Morgan E.D. J. Insect Physiol. 17:1971;969
12. (c) Butterworth J.H., Morgan E.D., Percy G.R. J. Chem. Soc., Perkin Trans. 1. 1972;2445
13. (d) Morgan E.D., Butterworth J.H. Phytochemistry. 12:1973;391.
14. (a) Kraus W., Bokel M., Klenk A., Pöhnl H. Tetrahedron Lett. 26:1985;6435
15. (b) Broughton H.B., Ley S.V., Slawin A.M.Z., Williams D.J., Morgan E.D. J. Chem. Soc., Chem. Commun. 1986;46
16. (c) Turner C.J., Tempesta M.S., Taylor R.B., Zagorski M.G., Termini J.S., Schroeder D.R., Nakanishi K. Tetrahedron. 43:1987;2789.
17. Ley S.V., Lovell H., Williams D.J. J. Chem. Soc., Chem. Commun. 1992;1304.
18. (a) Ley S.V., Denholm A.A., Wood A. Nat. Prod. Rep. 1993;109. and references cited therein
19. (b) Nishikimi Y., Iimori T., Sodeoka M., Shibasaki M. J. Org. Chem. 54:1989;3354
20. (c) Henry K.J. Jr., Fraser-Reid B. J. Org. Chem. 59:1994;5128
21. (d) Watanabe H., Watanabe T., Mori K. Tetrahedron. 52:1996;13939
22. (e) Watanabe H., Watanabe T., Mori K., Kitahara K. Tetrahedron Lett. 38:1997;4429
23. (f) Scheliger H., Winterfeldt E. Chirality. 9:1997;454
24. (g) Haag D., Chen X.-T., Fraser-Reid B. Chem. Commun. 1998;2577
25. (h) Ley S.V., Gutteridge C.E., Pape A.R., Spilling C.D., Zumbrunn C. Synlett. 1999;1295
26. (i) Nicolaou K.C., Follmann M., Roecker A.J., Hunt K.W. Angew. Chem. Int. Ed. 41:2002;2103
27. (j) Nicolaou K.C., Roecker A.J., Follmann M., Baati R. Angew. Chem. Int. Ed. 41:2002;2107
28. (k) Durand-Reville T., Gobbi L.B., Gray B.L., Ley S.V., Scott J.S. Org. Lett. 4:2002;3847
29. (l) Nicolaou K.C., Roecker A.J., Monenschein H., Guntupalli P., Follmann M. Angew. Chem. Int. Ed. 42:2003;3637.
30. (a) Simmonds M.S., Blaney W.M., Grossman R.B., Ley S.V. J. Insect Physiol. 41:1995;555
31. (b) Nisbet A.J., Mordue (Luntz) A.J., Grossman R.G., Jennens L., Ley S.V., Mordue W. Arch. Insect Biochem. Physiol. 46:2001;78.
32. Yamasaki B., Kloche J.A. J. Agric. Food Chem. 35:1987;467.
33. Ley S.V., Anderson J.C., Blaney W.M., Jones P.S., Lidert Z., Morgan E.D., Robinson N.G., Santafianos D., Simmonds M.S.J., Toogood P.L. Tetrahedron. 45:1989;5175.
34. Ley V.S., Santafianos D., Blaney W.M., Simmonds M.S.J. Tetrahedron Lett. 28:1987;221.
35. (a) Baldoni H.A., Enriz R.D., Jáuregui E.A., Csizmadia I.G. J. Mol. Struct. (Theochem). 363:1996;167
36. (b) Baldoni H.A., Enriz R.D., Csizmadia I.G. J. Mol. Struct. (Theochem). 463:1999;251
37. (c) Enriz R.D., Baldoni H.A., Zamora M.A., Jáuregui E.A., Sosa M.E., Tonn C.E., Luco J.M., Gordaliza M. J. Agric. Food Chem. 48:2000;1384.
38. (a) Kanoh N., Ishihara J., Murai A. Synlett. 1995;895
39. (b) Kanoh N., Ishihara J., Murai A. Synlett. 1997;737
40. (c) Ishihara J., Fukuzaki T., Murai A. Tetrahedron Lett. 40:1999;1907
41. (d) Ishihara J., Yamamoto Y., Kanoh N., Murai A. Tetrahedron Lett. 40:1999;4387
42. (e) Kanoh N., Ishihara J., Yamamoto Y., Murai A. Synthesis. 2000;1878
43. (f) Yamamoto Y., Ishihara J., Kanoh N., Murai A. Synthesis. 2000;1894.
44. Fukuzaki T., Kobayashi S., Hibi T., Ikuma Y., Ishihara J., Kanoh N., Murai A. Org. Lett. 4:2002;2877.
45. (a) Ishizumi K., Koga K., Yamada S. Chem. Pharm. Bull. 16:1968;492
46. (b) Itaya T., Fujii T., Evidente A., Randazzo G., Surico G., Iacobellis N. Tetrahedron Lett. 27:1986;6349.
47. (a) Barton D.H.R., McCombie S.W. J. Chem. Soc., Perkin Trans. I. 1975;1574
48. (b) Barton D.H.R., Motherwell W.B., Stange A. Synthesis. 1981;743.
49. Barton D.H.R., Jang D.O., Jaszberenyi J.C. Tetrahedron. 49:1993;7193.
50. (a) Ireland R.E., Muchmore D.C., Hengartner U. J. Am. Chem. Soc. 94:1972;5098
51. (b) Rigby J.H. Tetrahedron Lett. 23:1982;1863
52. (c) Trost B.M., Renaut P. J. Am. Chem. Soc. 104:1982;6668
53. (d) Wender P.A., von Geldern T.W., Levine B.H. J. Am. Chem. Soc. 110:1988;4858
54. (e) Boukouvalas J., Cheng Y.-X., Robichaud J. J. Org. Chem. 63:1998;228.
55. Liu H.-J., Shang S. Tetrahedron Lett. 39:1998;367.
56. (a) Hutchins B.O., Maryanoff B.E., Milewski C.A. J. Chem. Soc., Chem. Commun. 1971;1097
57. (b) Hutchins B.O., Kandasamy D., Maryanoff C.A., Masilamani C.D., Maryanoff B.E. J. Org. Chem. 42:1977;82.
58. Hutchins B.O., Kandasamy D., Dux F., Maryanoff C.A., Rotstein D., Goldsmith B., Burgoyne W., Cistone F., Dalessandro J., Puglis J. J. Org. Chem. 43:1978;2259.
59. (a) Corey E.J., Suggs J.W. J. Org. Chem. 38:1973;3224
60. (b) Corey E.J., Suggs J.W. Tetrahedron Lett. 1975;3775.
61. (a) Crabtree R.H., Felkin H., Morris E.E. J. Organometal. Chem. 141:1977;205
62. (b) Baudry D., Ephritikhine M., Felkin H. J. Chem. Soc., J. Chem. Commun. 1978;694.
63. (a) Breslow R., Baldwin S.W. J. Am. Chem. Soc. 92:1970;732
64. (b) Baldwin J.E., Bhatnagar A.K., Harper R.W. J. Chem. Soc., J. Chem. Commun. 1970;659.
65. Deleris G., Dunogues J., Gadras A. Tetrahedron. 44:1988;4243.
66. The stereochemstry of 15 was determined by its NOE correlation.
67. Noller H., Andréu P., Hunger M. Angew. Chem., Int. Ed. Engl. 10:1971;172.
68. Luche J.-L., Gemal A.L. J. Am. Chem. Soc. 101:1979;5848.
69. Anderson J.C., Ley S.V., Santafianos D., Sheppard R.N. Tetrahedron. 47:1991;6813.