Concise enantioselective synthesis of the ten-membered lactone cephalosporolide G and its C-3 epimer

Chemistry - A European Journal

Volumn 15, Issue 37, 2009, Pages 9286-9289

  Barradas, Silvia ^a   Urbano, Antonio ^a   Carreño, M Carmen ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Epoxidation; Lactones; Oxidative cleavage; Oxidative dearomatization; Total synthesis

Indexed keywords

DIASTEREOISOMERS; ENANTIOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE TOTAL SYNTHESIS; ENZYMATIC RESOLUTIONS; LACTONES; MACROLACTONES; NATURAL PRODUCTS; NATURALLY OCCURRING; ONE STEP; OXIDATIVE CLEAVAGE; OXIDATIVE CLEAVAGES; OXIDATIVE DEAROMATIZATION; PYRIDINIUM CHLOROCHROMATE; SINGLET OXYGEN; STEREO-SELECTIVE; SULFONIC ACID; TOTAL SYNTHESIS;

PHENOLS; TOLUENE;

OXYGEN;

CEPHALOSPOROLIDE G; LACTONE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

LACTONES; STEREOISOMERISM;

EID: 70349280229     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901735     Document Type: Article

References (47)

1. a) G. Rousseau, Tetrahedron 1995, 51, 2777-2849;
2. b) L. S. Longo, Jr., F.I. Bombonato, H. M. C Ferraz, Quim. Nova 2007, 30, 415-424;
3. c) I. Shiina, Chem. Rev. 2007, 107, 239-273;
4. d) H. M. C. Ferraz, F.I. Bombonato, M. K. Sano, L. S. Longo, Jr., Quim. Nova 2008, 32, 885-900.
5. For reviews, see: a) G. Dräger, A. Kirschning, R. Thiericke, M. Zerlin, Nat. Prod. Rep. 1996, 13, 365-375;
6. b) M. C. Ferraz, F. I. Bombonato, L. S. Longo, Jr., Synthesis 2007, 3261-3285;
7. c) V. B. Riatto, R. A. Pilli, M. M. Victor, Tetrahedron 2008, 64, 2279-2300.
8. a) G. Illuminati, L. Mandolini, Ace. Chem. Res. 1981, 14, 95-102;
9. b) L. Mandolini, Adv. Phys. Org. Chem. 1986, 22, 1-111;
10. c) C. G. Kreiter, K. Lehr, M. Leyendecker, W. S. Sheldrik, R. Exner, Chem. Ber. 1991, 124,3-11.
11. For a general review, see: A. Parenty, X. Moreau, J.-M. Campagne, Chem. Rev. 2006, 106, 911-939.
12. 32-45% yield; for examples, see: a) M. B. Andrus, T-L. Shih, J. Org. Chem. 1996, 61, 8780-8785;
13. b) R Radha Krishna, P. V. Narasimha Reddy, Tetrahedron Lett. 2006, 47, 7473-7476;
14. c) Y. Kobayashi, S. Yoshida, M. Asano, A. Takeuchi, H. R Acharya, J. Org. Chem. 2007, 72, 1707-1716;
15. d) R Gupta, R Kumar, Eur. J. Org. Chem. 2008, 1195-1202.
16. For recent reviews, see: a) A. Gradillas, J. Pérez-Castells, Angew. Chem. 2006, 118, 6232-6247;
17. Angew. Chem. Int. Ed. 2006, 45, 6086-6101;
18. b) K. C. Nicolaou, R G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4564-4601;
19. Angew. Chem. Int. Ed. 2005, 44, 4490-4527 K;
20. c) R. H. Grubbs, Tetrahedron 2004, 60, 7117-7140;
21. d) S. J. Connon, S. Blechert, Angew. Chem. 2003, 115, 1944-1968;
22. Angew. Chem. Int. Ed. 2003, 42, 1900-1923;
23. e) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172;
24. Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
25. D. K. Mohapatra, D. K. Ramesh, M. A. Giardello, M. S. Chorghade, M. K. Gurjar, R. H. Grubbs, Tetrahedron Lett. 2007, 48, 2621-2625, and references therein.
26. See refs. [2b], [2c] and [5d], and the following: a) C. V. Ramana, T. R Khaladkar, S. Chatterjee, M. K. Gurjar, J. Org. Chem. 2008, 73, 3817-3822;
27. b) J. Liu, L. Zhang, J. He, L. He, B. Ma, X. Pana, X. She, Tetrahedron: Asymmetry 2008, 19, 906-911;
28. c) M. Matsuda, T. Yamazaki, K.-I. Fuhshuku, T. Sugai, Tetrahedron 2007, 63, 8752-8760;
29. d) S. Ghosh, R. V. Rao, Tetrahedron Lett. 2007, 48, 6937-6940;
30. e) P. R. Krishna, M. Narsingam, Synthesis 2007, 3627-3634.
31. a) A. Farocq, J. Gordon, J. R. Hanson, J. A. Takahashi, Phytochemistry 1995, 38, 557-558;
32. b) M. J. Ackland, J. R. Hanson, P. B. Hitchcock, A. H. Ratcliffe, J. Chem. Soc. Perkin Trans. 1 1985, 843-847;
33. c) V. Rukachaisirikul, S. Pramjit, Ch. Pakawatchai, M. Isaka, S. Supothina, J. Nat. Prod. 2004, 67, 1953-1955.
34. R R. Krishna, A. Sreeshailam, Synlett 2008, 2795-2798.
35. Y. Yuasa, S. Shibuya, Y. Yuasa, Synth. Commun. 2003, 33, 1469-1475.
36. M. C. Carrefio, M. González-López, A. Urbano, Angew. Chem. 2006, 118, 2803-2807;
37. Angew. Chem. Int. Ed. 2006, 45, 2737-2741.
38. S. Barradas, M. C. Carrefio, M. González-López, A. Latorre, A. Urbano, Org. Lett. 2007, 9, 5019-5022.
39. a) H. M. C. Ferraz, L. S. Longo, Jr., J. Org. Chem. 2007, 72, 2945-2950;
40. b) H. M. C. Ferraz, L. S. Longo, Jr., Org. Lett. 2003, 5, 1337-1339.
41. a) G. H. Posner, M. A. Hatcher, W. A. Maio, Org. Lett. 2005, 7, 4301-4303;
42. b) M. A. Hatcher, K. Borstnik, G. H. Posner, Tetrahedron Lett. 2003, 44, 5407-5409.
43. R Wipf, W. Li, J. Org. Chem. 1999, 64, 4576-4577.
44. M. Honzumi, K. Ogasawara, Tetrahedron Lett. 2002, 43, 1047-1049.
45. CCDC-725048, 725049 and 725050 for 2, 10 and 14, respectively, contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/ cif.
46. a)T. Ooi, K. Maruoka, Rev. Heteroat. Chem. 1998, 18, 61-85;
47. b) K. Maruoka, Y. Araki, H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 2650-2652.