New development of Meyers' methodology: Stereoselective preparation of an axially chiral 5,7-fused bicyclic lactam related to circumdatins/benzomalvins and asperlicins

Tetrahedron Asymmetry

Volumn 17, Issue 2, 2006, Pages 281-286

  Penhoat, Maël ^a   Bohn, Pierre ^a   Dupas, Georges ^a   Papamicaël, Cyril ^a   Marsais, Francis ^a   Levacher, Vincent ^a  

^a UNIVERSITÉ ET INSA DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 FORMYL 4 OXO 4H QUINAZOLIN 3 YL)BENZOIC ACID; 2 (2 FORMYL 4 OXO 4H QUINAZOLIN 3 YL)BENZOIC ACID ETHYL ESTER; 2 (2 METHYL 4 OXO 4H QUINAZOLIN 3 YL)BENZOIC ACID; 2 (2 METHYL 4 OXO 4H QUINAZOLIN 3 YL)BENZOIC ACID ETHYL ESTER; 2 METHYL 3,1 BENZOXAZIN 4 ONE 4; ASPERLICIN; ASPERLICIN C; BENZODIAZEPINE; BENZOMALVIN A; BENZOMALVIN B; BENZOMALVIN C; CARBOXYLIC ACID; CIRCUMDATIN A; CIRCUMDATIN B; CIRCUMDATIN C; CIRCUMDATIN D; CIRCUMDATIN E; CIRCUMDATIN F; CIRCUMDATIN G; LACTAM DERIVATIVE; N ETHYL 2 FLUORO PYRIDINIUM TETRAFLUOROBORATE; N METHYL 2 CHLOROPYRIDINIUM IODIDE; QUINAZOLINONE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DEHYDRATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 32444449205     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.12.019     Document Type: Article

References (39)

1. K. Tsuyoshi, S. Yoshihiro, and M. Miwako Tetrahedron 60 2004 9649 9657
2. N. Langlois, A. Rojas-Rousseau, C. Gaspard, G.H. Werner, F. Darro, and R. Kiss J. Med. Chem. 44 2001 3754 3757
3. D.R. Langley, and D.E. Thurston J. Org. Chem. 52 1987 91 97
4. Q. Huang, X. He, C. Ma, R. Liu, S. Yu, C.A. Dayer, G.R. Wenger, R. McKernan, and J.M. Cook J. Med. Chem. 43 2000 71 95
5. L. Rahbæk, J. Breinholt, J.C. Frisvad, and C. Christophersen J. Org. Chem. 64 1999 1689 1692
6. L. Rahbæk, and J. Breinholt J. Nat. Prod. 62 1999 904 905
7. J.-R. Dai, B.K. Carté, P.J. Sidebottom, A.L.S. Yew, S.-B. Ng, Y. Huang, and M.S. Butler J. Nat. Prod. 64 2001 125 126
8. H.H. Sun, C.J. Barrow, D.M. Sedlock, A.M. Gillum, and R. Cooper J. Antibiot. 47 1994 515 522
9. H.H. Sun, C.J. Barrow, and R. Cooper J. Nat. Prod. 58 1995 1575 1580
10. M.A. Goetz, M. Lopez, R.L. Monaghan, R.S.L. Chang, V.J. Lotti, and T.B. Chen J. Antibiot. 38 1985 1633 1637
11. J.M. Liesh, O.D. Hensens, D.L. Zink, and M.A. Goetz J. Antibiot. 41 1988 878 881
12. B.K. Joshi, J.B. Gloer, D.T. Wicklow, and P.F. Dowd J. Nat. Prod. 62 1999 650 652
13. G. Bringmann, C. Günther, M. Ochse, O. Schupp, and S. Tasler W. Herz H. Falk G.W. Kirby R.E. Moore Progress in the Chemistry of Organic Natural Products 82 2001 Springer Wien, New York pp 3-249
14. For leading references on chiral bicyclic lactams see: A.I. Meyers, and G.P. Brengel Chem. Commun. 1997 1 8
15. M. Amat, M. Canto, N. Llor, V. Ponzo, M. Pérez, and J. Bosch Angew. Chem., Int. Ed. 41 2002 335 338
16. M. Amat, M. Canto, N. Llor, C. Escolano, E. Molins, E. Espinosa, and J. Bosch J. Org. Chem. 67 2002 5343 5351
17. M. Amat, N. Llor, J. Hidalgo, C. Escolano, and J. Bosch J. Org. Chem. 68 2003 1919 1928
18. M.D. Ennis, R.L. Hoffman, N.B. Ghazal, D.W. Old, and P.A. Mooney J. Org. Chem. 61 1996 5813 5817
19. S.M. Allin, S.L. James, M.R.J. Elsegood, and W.P. Martin J. Org. Chem. 67 2002 9464 9467
20. M. Penhoat, V. Levacher, and G. Dupas J. Org. Chem. 68 2003 9517 9520
21. Total synthesis of asperlicins: F. He, B.M. Foxman, and B.B. Snider J. Am. Chem. Soc. 120 1998 6417 6418
22. Total synthesis of Benzomalvins A and B: T. Sugimori, T. Okawa, S. Eguchi, A. Kakehi, E. Yashima, and Y. Okamoto Tetrahedron 54 1998 7997 8008
23. Total synthesis of benzomalvin C: H.H. Sun, C.J. Barrow, and R. Cooper J. Nat. Prod. 58 1995 1575 1580
24. Total synthesis of circumdatins F and C: A. Witt, and J. Bergman J. Org. Chem. 66 2001 2784 2788
25. Total synthesis of Sclerotigenin: D.R. Harrison, P.D. Kennewell, and J.B. Taylor J. Heterocycl. Chem. 14 1977 1191 1196
26. Building block approach: A. Grieder, and A.W. Thomas Synthesis 11 2003 1707 1711
27. L.A. Errede J. Org. Chem. 41 1976 1763 1765
28. G. Heller, and G. Fiesselman Justus Liebigs Ann. Chem. 324 1902 134
29. M.T. Bogert, and V.J. Chambers J. Am. Chem. Soc. 27 1905 649 658
30. N.C. Patel, and A.G. Mehta J. Indian Council Chem. 18 2001 83 86
31. 2 see: R.H. Baker, and R.N. Maxson Inorg. Synth. 1 1939 119
32. Organic reaction Vol. V 1952 Wiley London pp 345-346
33. The relative configuration in trans-(aS,R,S)-1 was determined by assuming the same sense of stereoselection as observed previously with related substrates and under the same reaction conditions, see Ref. 8.
34. M. Penhoat, S. Leleu, G. Dupas, C. Papamicaël, F. Marsais, and V. Levacher Tetrahedron Lett. 46 2005 8385 8389
35. K. Saigo, M. Usui, K. Kikushi, E. Shimada, and T. Mukaiyama Bull. Chem. Soc. Jpn. 50 1977 1863 1866
36. T. Mukaiyama Angew. Chem., Int. Ed. 18 1979 707 721
37. J.K. Sutherland, and D.A. Widdowson J. Chem. Soc. 1964 4650 4651
38. E. Bald, K. Saigo, and T. Mukaiyama Chem. Lett. 1975 1163 1166
39. P. Li, and J.-C. Xu Tetrahedron 56 2000 8119 8131