A short approach to the bicyclo[4.3.0]nonane fragment of stawamycin

Tetrahedron Letters

Volumn 46, Issue 26, 2005, Pages 4427-4431

  Dias, Luiz C ^a   Melgar, Gliseida Z ^a   Jardim, Luciana S A ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Intramolecular Diels Alder reaction; Lactone; Pyrroloketoindane family; Stille coupling

Indexed keywords

3 HYDROXY 2 METHYLPROPIONIC ACID METHYL ESTER; BICYCLO COMPOUND; PALLADIUM; PROPIONIC ACID DERIVATIVE; PYRROLE DERIVATIVE; STAWAMYCIN; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYL IODIDE; VINYL STANNANE;

ARTICLE; CATALYSIS; CATALYST; CYCLOADDITION; DIELS ALDER REACTION; DRUG SYNTHESIS; ISOMER; STILLE REACTION;

BETULACEAE;

EID: 19544391018     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.004     Document Type: Article

References (42)

1. R.B. Belshe Textbook of Human Virology 2nd ed. 1991 Mosby-Year Book St. Louis 862 888 Chapter 36
2. P.M. Lieberman, and A.J. Berk J. Virol. 64 1990 2560
3. Y.-N. Chang, D.L.-Y. Dong, G.S. Hayward, and S.D. Hayward J. Virol. 64 1990 3358
4. N.J. Dimmock, and S.B. Primrose Introduction to Modern Virology 4th ed. 1994 Blackwell Science Oxford 266 267 Chapter 17
5. S. Miao, M.R. Anstee, V. Baichwal, and A. Park Tetrahedron Lett. 36 1995 5699
6. Pyrroloketoindanes are named according to their pyrrole part. This family of natural products also includes indanomycin (X-14547A), 16-deethylindanomycin (A83094A), homoindanomycin and cafamycin
7. The numbering of 1 as well as of each intermediate follows that suggested in Ref. 2
8. R.M. Williams, and E.M. Stocking Angew. Chem., Int. Ed. 42 2003 3078
9. L.C. Dias, L.S.A. Jardim, A.A. Ferreira, and H.U. Soarez J. Braz. Chem. Soc. 12 2001 463
10. For similar intramolecular Diels-Alder approaches, see: S.D. Burke, A.D. Piscopio, M.E. Kort, M.A. Matulenko, M.H. Parker, D.M. Armistead, and K. Shankaran J. Org. Chem. 59 1994 332
11. M.P. Edwards, S.V. Ley, S.G. Lister, B.D. Palmer, and D.J. Williams J. Org. Chem. 59 1984 3503
12. W.R. Roush, and A.G. Myers J. Org. Chem. 46 1981 1509
13. W.R. Roush, and S.M. Peseckis Tetrahedron Lett. 23 1982 4879
14. M.P. Edwards, S.V. Ley, S.G. Lister, B.D. Palmer, and D.J. Williams Tetrahedron Lett. 22 1981 361
15. S.D. Burke, D.M. Armistead, and K. Shankaran Tetrahedron Lett. 27 1986 6295
16. K.C. Nicolaou, and R.L. Magolda J. Org. Chem. 46 1981 1506
17. M.P. Edwards, S.V. Ley, S.G. Lister, and B.D. Palmer J. Chem. Soc., Chem. Commun. 1983 630
18. K.C. Nicolaou, A.P. Patron, K. Ajito, P.K. Richter, H. Khatuya, P. Bertinato, R.A. Miller, and M.J. Tomaszewski Chem. Eur. J. 2 1996 847
19. T. Kawabata, Y. Kimura, T. Ito, and S. Terashima Tetrahedron 44 1988 2149
20. P.M. Smith, and E.J. Thomas J. Chem. Soc., Perkin Trans. 1 1998 3541
21. 4 reduction followed by Swern oxidation, in 87% overall yield
22. L.C. Dias, and P.L. Campano J. Braz. Chem. Soc. 9 1998 97
23. D.A. Evans, and J.S. Johnson J. Org. Chem. 62 1997 786
24. D.A. Evans, K.A. Scheidt, and C.W. Downey Org. Lett. 3 2001 3009
25. D.A. Claremon, and R.E. Dolle III J. Am. Chem. Soc. 103 1981 6967
26. S.S.C. Koch, and A.R. Chamberlin J. Org. Chem. 58 1993 2725
27. K. Horita, T. Yoshioka, T. Tanaka, Y. Oikawa, and O. Yonemitsu Tetrahedron 42 1986 3021
28. For alcohol 15a, oxidation must be done immediately after deprotection in order to avoid formation of the product from intramolecular Michael addition reaction
29. K. Takai, K. Nitta, and K. Utimoto J. Am. Chem. Soc. 108 1986 7408
30. I. Paterson, H. Lombart, and C.M.N. Allerton Org. Lett. 1 1999 19
31. Y. Araki, and T. Konoike J. Org. Chem. 62 1997 5299
32. P.A. Wender, S.M. Sieburth, J.J. Petraotis, and S.K. Singh Tetrahedron 37 1981 3967
33. J. Ishihara, T. Sugimoto, and A. Murai Tetrahedron 53 1997 16029
34. S.R. Chemler, U. Iserloh, and S.J. Danishefsky Org. Lett. 3 2001 2949
35. H. Sugiyama, and F. Yokokawa Org. Lett. 2 2000 2149
36. J.K. Stille Angew. Chem., Int. Ed. Engl. 25 1986 508
37. V. Farina Pure Appl. Chem. 68 1996 73
38. A.J. Duncton, and G. Pattenden J. Chem. Soc., Perkin Trans. 1 1999 1235
39. J.K. Stille, and B.L. Groh J. Am. Chem. Soc. 109 1987 813
40. L.C. Dias J. Braz. Chem. Soc. 8 1997 289
41. T.J. Brocksom, J. Nakamura, M.L. Ferreira, and U. Brocksom J. Braz. Chem. Soc. 12 2001 597
42. 13C NMR, IR, HRMS and analytical data. Yields refer to chromatographically and spectroscopically homogeneous materials