Enantio- and diastereocontrolled total synthesis of (+)-strictifolione

European Journal of Organic Chemistry

Volumn , Issue 36, 2010, Pages 6993-7004

  Kumar, Pradeep ^a   Pandey, Menaka ^a   Gupta, Priti ^a   Naidu, S Vasudeva ^a   Dhavale, Dilip D ^b  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b UNIVERSITY OF PUNE   (India)

Author keywords

Asymmetric synthesis; Hydrolytic kinetic resolution; Lactones; Natural products; Organocatalysis; Ring closing metathesis; Total synthesis

Indexed keywords

EID: 78650099772     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001221     Document Type: Article

References (63)

1. H. M. R. Hoffmann, J. Rabe, Angew. Chem. Int. Ed. Engl. 1985, 24, 94-110.
2. Juliawaty, M. Kitajima, H. Takayama, S. A. Achmad, N. Aimi, Phytochemistry 2000, 54, 989-993.
3. For reviews about naturally occurring 6-substituted 5,6-dihydro-α- pyrones, see
4. M. T. Davies-Coleman, D. E. A. Rivett, in: Fortschritte der Chemie Organischer Naturstoffe, vol. 55 (Eds.:, W. Herz, H. Grisebach, G. W. Kirby, C. Tamm), Springer-Verlag, Wien, New York, 1989.
5. J. L. A. Collett, M. T. Davies-Coleman, D. E. A. Rivett, in: Fortschritte der Chemie Organischer Naturstoffe, vol. 75 (Eds.:, W. Herz, H. Falk, G. W. Kirby, R. E. Moore, C. Tamm), Springer-Verlag, Wien, New York, 1998.
6. J. A. Marco, M. Carda, J. Murga, E. Falomir, Tetrahedron 2007, 63, 2929-2958.
7. V. Boucard, G. Broustal, J. M. Campagne, Eur. J. Org. Chem. 2007, 225-236.
8. S. D. Rychnovsky, Chem. Rev. 1995, 95, 2021-2040.
9. M. Kalesse, M. Christmann, Synthesis 2002, 981-1003.
10. G. E. Raoelison, C. Terreaux, E. F. Queiroz, F. Zsila, M. Simonyi, S. Antus, A. Randriantsoa, K. Hostettmann, Helv. Chim. Acta 2001, 84, 3470-3476.
11. F. Echeverri, V. Arango, W. Quiñones, F. Torres, G. Escobar, Y. Rosero, R. Archbold, Phytochemistry 2001, 56, 881-885.
12. S. Kobayashi, K. Tsuchiya, T. Harada, M. Nishide, T. Kurokawa, T. Nakagawa, N. Shimada, K. Kobayashi, J. Antibiot. 1994, 47, 697-702.
13. S. Kobayashi, K. Tsuchiya, T. Kurokawa, T. Nakagawa, N. Shimada, Y. Iitaka, J. Antibiot. 1994, 47, 703-707.
14. K. Tsuchiya, S. Kobayashi, T. Harada, T. Nishikiori, T. Nakagawa, K. Tatsuta, J. Antibiot. 1997, 50, 259-260.
15. B. Jiang, Z. Chen, Tetrahedron: Asymmetry 2001, 12, 2835-2843. and references cited therein.
16. G. C. Hokanson, J. C. French, J. Org. Chem. 1985, 50, 462-466.
17. W. Scheithauer, D. D. Von Hoff, G. M. Clark, J. L. Shillis, E. F. Elslager, Eur. J. Cancer Clin. Oncol. 1986, 22, 921-926.
18. D. W. Fry, T. J. Boritzki, R. C. Jackson, Cancer Chemother. Pharmacol. 1984, 13, 171-175.
19. W. R. Leopold, J. L. Shillis, A. E. Mertus, J. M. Nelson, B. J. Roberts, R. C. Jackson, Cancer Res. 1984, 44, 1928-1932.
20. L. D. Juliawaty, Y. Watanabe, M. Kitajima, S. A. Achmad, H. Takayama, N. Aimi, Tetrahedron Lett. 2002, 43, 8657-8660.
21. C. V. Ramana, N. Raghupathi, M. K. Gurjar, M. S. Chorghade, Tetrahedron Lett. 2005, 46, 4073-4075.
22. G. Sabitha, N. Fatima, P. Gopal, C. N. Reddy, J. S. Yadav, Tetrahedron: Asymmetry 2009, 20, 184-191.
23. J. Cossy, S. BouzBouz, A. H. Hoveyda, Org. Lett. 2003, 5, 1995-1997.
24. D. Enders, A. Lenzen, M. Müller, Synthesis 2004, 9, 1486-1496.
25. S.-Y. Tosaki, Y. Horiuchi, T. Nemoto, T. Ohshima, M. Shibasaki, Chem. Eur. J. 2004, 10, 1527-1544.
26. P. Kumar, S. V. Naidu, P. Gupta, J. Org. Chem. 2005, 70, 2843-2846.
27. P. Kumar, S. V. Naidu, J. Org. Chem. 2005, 70, 4207-4210.
28. P. Gupta, S. V. Naidu, P. Kumar, Tetrahedron Lett. 2005, 46, 6571-6573.
29. P. Kumar, P. Gupta, S. V. Naidu, Chem. Eur. J. 2006, 12, 1397-1402.
30. P. Kumar, S. V. Naidu, J. Org. Chem. 2006, 71, 3935-3941.
31. P. Gupta, P. Kumar, Eur. J. Org. Chem. 2008, 1195-1202.
32. P. S. Chowdhury, P. Gupta, P. Kumar, Tetrahedron Lett. 2009, 50, 7018-7020.
33. M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938.
34. S. E. Schaus, J. Branalt, E. N. Jacobson, J. Org. Chem. 1998, 63, 4876-4877.
35. J. M. Keith, J. F. Larrow, E. N. Jacobsen, Adv. Synth. Catal. 2001, 343, 5-26.
36. S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315.
37. For a review on the application of hydrolytic kinetic resolution (HKR), see:, P. Kumar, S. V. Naidu, P. Gupta, Tetrahedron 2007, 63, 2745-2785.
38. P. Kumar, P. Gupta, Synlett 2009, 1367-1382.
39. N. B. Kondekar, P. Kumar, Org. Lett. 2009, 11, 2611-2614.
40. R. Noyori, Pure Appl. Chem. 1981, 53, 2315-2322.
41. R. Noyori, I. Tomino, Y. Tanimoto, M. Nishizawa, J. Am. Chem. Soc. 1984, 106, 6709-6716.
42. For the HKR of racemic 4-phenylbutylene oxide using Jacobsen's R,R-(salen)Co catalyst, see
43. J. G. Martynow, J. Jówik, W. Szelejewski, O. Achmatowicz, A. Kutner, K. Winiewski, J. Winiarski, O. Zegrocka-Stendel, P. Gołbiewski, Eur. J. Org. Chem. 2007, 689-703.
44. Raj, I. V. Paul, A. Sudalai, Tetrahedron Lett. 2008, 49, 2646-2648.
45. K. C. Nicolaou, S. E. Webber, Synthesis 1986, 453-461.
46. K. Takao, H. Ochiai, K. Yoshida, T. Hashizuka, H. Koshimura, K. Tadano, S. Ogawa, J. Org. Chem. 1995, 60, 8179-8193.
47. In order to determine the chiral purity of 25 it was converted into a lactone by treatment with pTsA in methanol HPLC: Kromasil 5-Amycoat column (EtOH/n-hexane) 25:75, flow rate: 0.7 mL/min, Î = 214 nm). Retention time [min]: 8.817 (major) and 10.092 (minor). The racemic standard was prepared in the same way with racemic γ-hydroxy ester, ee 98 %.
48. I. Izzo, S. D. Caro, F. De Riccardis, A. Spinella, Tetrahedron Lett. 2000, 41, 3975-3978.
49. K. Otaka, K. Mori, Eur. J. Org. Chem. 1999, 1795-1802.
50. Y. Deng, R. G. Salomon, J. Org. Chem. 2000, 65, 6660-6665.
51. K. E. Drouet, E. A. Theodorakis, Chem. Eur. J. 2000, 6, 1987-2001.
52. A. B. Smith III, G. R. Ott, J. Am. Chem. Soc. 1998, 120, 3935-3948.
53. A. B. Smith III, Z. J. Wan, J. Org. Chem. 2000, 65, 3738-3753.
54. For reviews on alkene cross-metathesis, see
55. S. J. Connon, S. Blechert, Angew. Chem. Int. Ed. 2003, 42, 1900-1923.
56. S. E. Gibson, S. P. Keen, Top. Organomet. Chem. 1999, 1, 155-181.
57. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. Int. Ed. 2005, 44, 4490-4527.
58. P. V. Ramachandran, G.-M. Chen, H. C. Brown, Tetrahedron Lett. 1997, 38, 2417-2420.
59. for a review on asymmetric allylborations, see:, P. V. Ramachandran, Aldrichim. Acta 2002, 35, 23.
60. For reviews on ring-closing metathesis, see
61. R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450.
62. J. Prunet, Angew. Chem. Int. Ed. 2003, 42, 2826-2830.
63. V. Rauniyar, H. Zhai, D. G. Hall, J. Am. Chem. Soc. 2008, 130, 8481-8490.