Synthetic studies on azadirachtin (Part 3): Asymmetric synthesis of the tricyclic dihydrofuran moiety of azadirachtin

Tetrahedron Letters

Volumn 40, Issue 10, 1999, Pages 1907-1910

  Ishihara, J ^a   Fukuzaki, T ^a   Murai, A ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Asymmetric Diels Alder reaction; Azadirachtin; Dihydrofuran

Indexed keywords

AZADIRACHTIN; COPPER; FURAN DERIVATIVE; OXAZOLINE DERIVATIVE; TRICYCLIC DIHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; SYNTHESIS;

BETULACEAE;

EID: 0033525661     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00040-4     Document Type: Article

References (23)

1. A. Murai R. Greenhalgh T.R. Roberts Pesticide Science and Biotechnology 1987 Blackwell London 81 88
2. J.N. Culver W.O. Dawson Molec. Plant-Microbe. Interact. 4 1991 458
3. G.F.J.M. Van den Ackerveken J.A.L. Van Kan P.J.G.M. Dewit Plant J. 2 1992 359
4. H.B. Broughton S.V. Ley Z. Lidert A.M.Z. Slawin D.J. Williams E.D. Morgan J. Chem. Soc., Chem. Commun. 1985 46
5. W. Kraus M. Bokel A. Klenk H. Pöhnl Tetrahedron Lett. 26 1985 6435
6. N. Kanoh J. Ishihara A. Murai SYNLETT 1995 895
7. N. Kanoh J. Ishihara A. Murai SYNLETT 1997 737
8. S.V. Ley A.A. Denholm A. Wood Nat. Prod. Rep. 1993 109 and references cited therein
9. Y. Nishikimi T. Iimori M. Sodeoka M. Shibasaki J. Org. Chem. 54 1989 3354
10. K.J. Henry Jr. B. Fraser-Reid J. Org. Chem. 59 1994 5128
11. H. Watanabe T. Watanabe K. Mori Tetrahedron 52 1996 13939
12. H. Watanabe T. Watanabe K. Mori T. Kitahara Tetrahedron Lett. 38 1997 4429
13. Recent review on aymmetric catalytic Diels-Alder reactions: R.E. Gawley J. Aubé J.E. Baldwin P.D. Magnus Tetrahedron Organic Chemistry Ser. Vol. 14 Principles of Asymmetric Synthesis 1996 Pergamon Oxford 277 285
14. For pioneering works on syntheses of natural products using asymmetric catalytic Diels-Alder reaction: E.J. Corey A. Guzman-Perez T.-P. Loh J. Am. Chem. Soc. 116 1994 3611
15. D.A. Evans J.S. Johnson J. Org. Chem. 62 1997 786
16. D.A. Evans S.J. Miller T. Lectka J. Am. Chem. Soc. 115 1993 6460
17. D.A. Evans T. Lectka S.J. Miller Tetrahedron Lett. 34 1993 7027
18. G.-J. Ho D.J. Mathre J. Org. Chem. 60 1995 2271
19. D.A. Evans T.C. Britton J.A. Ellman Tetrahedron Lett. 28 1987 6141
20. M. Vandewalle J. Van der Eycken W. Oppolzer C. Vullioud Tetrahedron 42 1986 4035
21. G.A. Molander Chem. Rev. 92 1992 29
22. J.C. Anderson S.C. Smith SYNLETT 1990 107
23. K.J. Henry Jr. P.A. Grieco C.T. Jagoe Tetrahedron Lett. 33 1992 1817