A highly stereocontrolled asymmetric total synthesis of epimer of (+)-7-deoxypancratistatin

Tetrahedron Letters

Volumn 54, Issue 41, 2013, Pages 5562-5566

  Chavan, Subhash P ^a   Garai, Sumanta ^a   Dey, Chandan ^a   Gonnade, Rajesh G ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

7 Deoxypancratistatin; Amaryllidaceous alkaloids; Deoxygenation; Epimer; Sharpless asymmetric dihydroxylation

Indexed keywords

7 DEOXYPANCRATISTATIN; ALKALOID DERIVATIVE; ANTIVIRUS AGENT; GRIGNARD REAGENT; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; BIRCH REDUCTION; BROMINATION; CHELATION; DEOXYGENATION; DIASTEREOISOMER; DIHYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; EPIMER; GRIGNARD REACTION; HYDROGENATION; HYDROGENOLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; PURIFICATION; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 84883488268     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.07.125     Document Type: Article

References (44)

1. J.L. Hartwell Lloydia 30 1967 379
2. G.R. Pettit, V. Gaddamidi, and G.M. Cragg J. Nat. Prod. 47 1984 1018
3. G.R. Pettit, V. Gaddamidi, G.M. Cragg, D.L. Herald, and Y. Sagawa J. Chem. Soc., Chem. Commun. 1984 1693
4. S. Ghosal, S. Singh, Y. Kumar, and R.S. Srivastava Phytochemistry 28 1989 611
5. T. Hudlicky, X. Tian, and K. Königsberger Synlett 1995 1125
6. G.E. Keck, S.F. McHardy, and J.A. Murry J. Am. Chem. Soc. 117 1995 7289
7. T. Hudlicky, X. Tian, K. Königsberger, R. Maurya, J. Rouden, and B. Fan J. Am. Chem. Soc. 118 1996 10752
8. G.E. Keck, T.T. Wager, and S.F. McHardy J. Org. Chem. 63 1998 9164
9. G.E. Keck, J.A. Murry, and S.F. McHardy J. Org. Chem. 64 1999 4465
10. H. Akgün, and T. Hudlicky Tetrahedron Lett. 40 1999 3081
11. J.L. Acena, O. Arjona, M.L. León, and J. Plumet Org. Lett. 2 2000 3683
12. T. Hudlicky, U. Rinner, D. Gonzalez, H. Akgun, S. Schilling, P. Siengalewicz, T.A. Martinot, and G.R. Pettit J. Org. Chem. 67 2002 8726
13. G. Pandey, A. Murugan, and M. Balakrishnan Chem. Commun. 2002 624
14. H. Zhang, and A. Padwa Tetrahedron Lett. 47 2006 3905
15. K.H. Shukla, D.J. Boehmler, S. Bogacyzk, B.R. Duvall, W.A. Peterson, W.T. McElroy, and P. DeShong Org. Lett. 8 2006 4183
16. A.E. Hakansson, A. Palmelund, H. Holm, and R. Madsen Chem. Eur. J. 12 2006 3243
17. A. Padwa, and H. Zhang J. Org. Chem. 72 2007 2570
18. G. Pandey, M. Balakrishnan, and P.S. Swaroop Eur. J. Org. Chem. 2008 2008 5839
19. G. Pandey, and M. Balakrishnan J. Org. Chem. 73 2008 8128
20. J. Collins, U. Rinner, M. Moser, T. Hudlicky, I. Ghiviriga, A.E. Romero, A. Kornienko, D. Ma, C. Griffin, and S. Pandey J. Org. Chem. 75 2010 3069
21. O. Nieto-Garcia, H. Lago-Santome, F. Cagide-Fagin, J.C. Ortiz-Lara, and R. Alonso Org. Biomol. Chem. 10 2012 825
22. U. Rinner, P. Siengalewicz, and T. Hudlicky Org. Lett. 4 2001 115
23. K.C. Nicolaou, T. Montagnon, P.S. Baran, and Y.L. Zhong J. Am. Chem. Soc. 124 2002 2245
24. K. Tanemura, T. Suzuki, Y. Nishida, K. Satsumabayashi, and T. Horaguchi Chem. Commun. 2004 470
25. E.N. Jacobsen, I. Marko, W.S. Mungall, G. Schroeder, and K.B. Sharpless J. Am. Chem. Soc. 110 1988 1968
26. H.C. Kolb, M.S. VanNieuwenhze, and K.B. Sharpless Chem. Rev. 94 1994 2483 and references therein
27. D.J. Cram, and K. Kopecky J. Am. Chem. Soc. 81 1959 2748
28. M. Reetz Angew. Chem., Int. Ed. 23 2003 556
29. J.L. Luche J. Am. Chem. Soc. 100 1978 2226
30. A.L. Gemal, and J.L. Luche J. Am. Chem. Soc. 103 1981 5454
31. M. Cherest, H. Felkin, and N. Prudent Tetrahedron Lett. 1968 2199
32. N.T. Anh, and O. Eisenstein Nouv. J. Chim. 1 1977 61
33. T. Nishikawa, M. Asai, N. Ohyabu, and M. Isobe J. Org. Chem. 63 1998 188
34. O. Mitsunobu, and M. Yamada Bull. Chem. Soc. Jpn. 40 1967 2380
35. O. Mitsunobu Synthesis 1981 1
36. For '1-aryl-1-deoxyconduritols F' see O.N. Nadein, and A. Kornienko Org. Lett. 6 2004 831
37. For review on conduritols see M. Balci, Y. Sütbeyaz, and H. Secen Tetrahedron 46 1990 3715
38. R. Webster, A. Boyer, M.J. Fleming, and M. Lautens Org. Lett. 12 2010 5418
39. M. Yoshida, T. Watanabe, and T. Ishikawa Tetrahedron Lett. 43 2002 6751
40. M.E. Krafft, and W.J. Crooks J. Org. Chem. 53 1988 432
41. M. Uemura, H. Nishimura, T. Minami, and Y. Hayashi J. Am. Chem. Soc. 113 1991 5402
42. G.H. Small, A.E. Minnella, and S.S. Hall J. Org. Chem. 40 1975 3151
43. X. Tian, T. Hudlicky, and K. Konigsberger J. Am. Chem. Soc. 117 1995 3643
44. M.G. Banwell, B.D. Bisset, S. Busato, C.J. Cowden, D.C.R. Hockless, J.W. Holman, R.W. Read, and A.W. Wu J. Chem. Soc., Chem. Commun. 1995 2551