Step-economic and protecting-group-free total synthesis of (+)-cardiobutanolide

Asian Journal of Organic Chemistry

Volumn 2, Issue 1, 2013, Pages 74-84

  Fernandes, Rodney A ^a   Kattanguru, Pullaiah ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

Asymmetric dihydroxylation; Cardiobutanolide; Cross metathesis; Natural products; Styryllactones

Indexed keywords

EID: 84898493860     PISSN: 21935807     EISSN: 21935807     Source Type: Journal    
DOI: 10.1002/ajoc.201200130     Document Type: Article

References (55)

1. A. Hisham, M. Toubi, W. Shuaily, M. D. A. Bai, Y. Fijimoto, Phytochemistry 2003, 62, 597.
2. F. R. Chang, J. L. Wei, C. M. Teng, Y. C. Wu, J. Nat. Prod. 1998, 61, 1457;
3. H. Yang, X. Li, Y. Tang, N. Zhang, J. Chen, B. Cai, J. Pharm. Biomed. Anal. 2009, 49, 140.
4. E. Pérez, J. Sáez, S. Blair, X. Franck, B. Figadère, Lett. Org. Chem. 2004, 1, 102;
5. C. A. Carollo, A. R. Hellmann-Carollo, J. M. Siqueira, S. Albuquerque, J. Chil. Chem. Soc. 2006, 51, 837;
6. D. B. Silva, M. F. C. Matos, S. T. Nakashita, C. K. Misu, N. C. Yoshida, C. A. Carollo, J. R. Fabri, H. S. Miglio, J. M. Siqueira, Quim. Nova 2007, 30, 1809;
7. S. Puvanendran, T. Manoranjan, A. Wickramasinghe, D. N. Karunaratne, V. Kumar, S. Wijesundara, G. Carr, R. Andersen, V. Karunaratne, J. Natl. Sci. Found. Sri Lanka 2010, 38, 75.
8. I. C. Moreira, J. H. G. Lago, N. F. Roque, Biochem. Syst. Ecol. 2005, 33, 948.
9. M. A. Blázquez, A. Bermejo, M. C. Zafra-Polo, D. Cortes, Phytochem. Anal. 1999, 10, 161;
10. H. B. Mereyala, M. Joe, Curr. Med. Chem. Anti-Cancer Agents 2001, 1, 293.
11. P. Ruiz, J. Murga, M. Carda, J. A. Marco, J. Org. Chem. 2005, 70, 713;
12. D. Matsuura, K. Takabe, H. Yoda, Tetrahedron Lett. 2006, 47, 1371;
13. P. RadhaKrishna, P. V. N. Reddy, Tetrahedron Lett. 2006, 47, 4627;
14. A. Garg, R. P. Singh, V. K. Singh, Tetrahedron 2006, 62, 11240;
15. K. R. Prasad, S. L. Gholap, J. Org. Chem. 2008, 73, 2916;
16. P. RadhaKrishna, E. S. Kumar, Tetrahedron Lett. 2009, 50, 6676;
17. J. S. Yadav, B. Madhavarao, K. S. Rao, Synlett 2009, 3179;
18. S. Chandrasekhar, N. Kiranmai, Tetrahedron Lett. 2010, 51, 4058;
19. P. Pal, A. K. Shaw, Tetrahedron 2011, 67, 4036.
20. R. W. Hoffmann, Synthesis 2006, 3531;
21. I. S. Young, P. S. Baran, Nat. Chem. 2009, 1, 193.
22. R. A. Fernandes, A. K. Chowdhury, J. Org. Chem. 2009, 74, 8826;
23. R. A. Fernandes, A. B. Ingle, Synlett 2010, 158;
24. R. A. Fernandes, S. V. Mulay, J. Org. Chem. 2010, 75, 7029;
25. R. A. Fernandes, S. V. Mulay, Synlett 2010, 2667;
26. R. A. Fernandes, A. B. Ingle, Tetrahedron Lett. 2011, 52, 458;
27. R. A. Fernandes, A. K. Chowdhury, Eur. J. Org. Chem. 2011, 1106;
28. R. A. Fernandes, P. Kattanguru, Tetrahedron: Asymmetry 2011, 22, 1930.
29. J. Song, R. I. Hollingsworth, Tetrahedron: Asymmetry 2001, 12, 387.
30. O. Andrey, J. Sperry, U. S. Larsen, M. A. Brimble, Tetrahedron 2008, 64, 3912.
31. For selected references on cross-metathesis, see:
32. A. K. Chatterjee, T. L. Choi, D. P. Sanders, R. H. Grubbs, J. Am. Chem. Soc. 2003, 125, 11360;
33. A. H. Hoveyda, P. J. Lombardi, R. V. O'Brien, A. R. Zhugralin, J. Am. Chem. Soc. 2009, 131, 8378;
34. K. Voigtritter, S. Ghorai, B. H. Lipshutz, J. Org. Chem. 2011, 76, 4697 and references therein.
35. S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168;
36. S. Gessler, S. Randl, S. Blechert, Tetrahedron Lett. 2000, 41, 9973.
37. [6f] However, the product could not be separated from the catalyst. After repetition of this reaction several times, we only obtained dimerization of 6a.
38. For reviews, see:
39. H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483;
40. C. Bolm, J. P. Hildebrand, K. Muniz in Catalytic Asymmetric Synthesis, 2nded. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, pp.399;
41. A. B. Zaitsev, H. Adolfsson, Synthesis 2006, 1725.
42. For CBS reduction, see:
43. E. J. Corey, E. C. J. Helal, Angew. Chem. 1998, 110, 2092; Angew. Chem. Int. Ed. 1998, 37, 1986;
44. J. Garcia, M. López, J. Romeu, Tetrahedron: Asymmetry 1999, 10, 2617.
45. 1HNMR spectroscopy. Assignment of the stereocenters was based on conversion of 9a into the final compound 1.
46. For dihydroxylation with NMO, see:
47. V. Vanrheenen, R. C. Kelly, D. Y. Cha, Tetrahedron Lett. 1976, 17, 1973;
48. L. Ahrgren, L. Sutin, Org. Process Res. Dev. 1997, 1, 425;
49. J. A. Gladding, J. P. Bacci, S. A. Shaw, A. B. Smith III, Tetrahedron 2011, 67, 6697.
50. For matched or mismatched stereoselectivity in double diastereoselection in asymmetric dihydroxylation of chiral olefin substrates, see ref.14a.
51. For a similar highly diastereoselective reduction, see ref.6d.
52. [6f] Reaction details were not available.
53. M. A. Delton, G. U. Yuen, J. Org. Chem. 1968, 33, 2473.
54. Z. Wang, Y. T. Cui, Z. B. Xu, J. Qu, J. Org. Chem. 2008, 73, 2270.
55. A provisional process patent on this work has been filed, application no. 1780/MUM/2012.