Synthesis of macrocyclic precursors of lankacidins using Stille reactions of 4-(2-iodo-alkenyl)azetidinones and related compounds for ring closure

Tetrahedron

Volumn 66, Issue 33, 2010, Pages 6613-6625

  Brain, Christopher T ^a   Chen, Anqi ^a   Nelson, Adam ^a   Tanikkul, Nongluk ^a   Thomas, Eric J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Chemoselectivity; Macrocyclization; Natural products; Palladium catalyzed coupling; Stereoselectivity; Total synthesis

Indexed keywords

4 (2 IODO ALKENYL)AZETIDINONE; ALDEHYDE; AZETIDINONE DERIVATIVE; HYDROXYL GROUP; LACTONE; LANKACIDIN; MACROCYCLIC COMPOUND; SULFONE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; PRECURSOR; PRIORITY JOURNAL; STEREOCHEMISTRY; STILLE REACTION; SYNTHESIS;

EID: 77955658404     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.129     Document Type: Article

References (50)

1. (a) M. Uramoto, N. Otake, L. Cary, and M. Tanabe J. Am. Chem. Soc. 100 1978 3616
2. (b) K. Kakinuma, J. Uzawa, and M. Uramoto Tetrahedron Lett. 23 1982 5303
3. (c) S. Harada, and T. Kishi Chem. Pharm. Bull. 22 1974 99
4. (d) S. Harada Chem. Pharm. Bull. 23 1975 2201
5. (e) M. Uramoto, N. Otake, Y. Ogawa, and H. Yonehara Tetrahedron Lett. 27 1969 2249
6. (f) K. Kamiya, S. Harada, Y. Wada, M. Nishikawa, and T. Kishi Tetrahedron Lett. 27 1969 2245
7. (g) S. Harada, J. Okada, M. Takeda, and T. Yamazi J. Antibiot. 38 1985 877
8. (a) K. Tsuchiya, T. Yamazaki, and Y. Takeuchi J. Antibiot. 24 1971 29
9. (b) K. Ootsu, T. Matsumoto, S. Harada, and T. Kishi Cancer Chemother. Rep., Part 1 59 1975 919
10. (a) K. Kakinuma Tetrahedron Lett. 23 1982 5303
11. (b) S. Tatsuno, K. Arakawa, and H. Kinashi J. Antibiot. 60 2007 700
12. (c) K. Arakawa, F. Sugino, K. Kodama, T. Ishii, and H. Kinashi Chem. Biol. 12 2005 249
13. A.S. Kende, K. Liu, I. Kaldor, G. Dorey, and K. Koch J. Am. Chem. Soc. 117 1995 8258
14. (a) E.J. Thomas, and A.C. Williams J. Chem. Soc., Perkin Trans. I 1995 351
15. (b) J.M. Roe, and E.J. Thomas J. Chem. Soc., Perkin Trans. I 1995 359
16. D.R. Williams, C.M. Rojas, and S.L. Bogen J. Org. Chem. 64 1999 736
17. E.G. Mata, and E.J. Thomas J. Chem. Soc., Perkin Trans. I 1995 785
18. (a) J.K. Stille Angew. Chem., Int. Ed. Engl. 25 1986 508
19. (b) J.K. Stille, and M. Tanaka J. Am. Chem. Soc. 109 1987 3785
20. (c) A. Kalivretenos, J.K. Stille, and L.S. Hegedus J. Org. Chem. 56 1991 2883
21. For preliminary communications on part of this work see: (a) C.T. Brain, A. Chen, A. Nelson, N. Tannikkul, and E.J. Thomas Tetrahedron Lett. 42 2001 1247
22. (b) A. Chen, A. Nelson, N. Tanikkul, and E.J. Thomas Tetrahedron Lett. 42 2001 1251
23. (a) M.L. Boys Tetrahedron Lett. 39 1998 3449
24. (b) A. Basak, and U.K. Khamrai Tetrahedron Lett. 37 1996 2475
25. T. Yamanaka, M. Ohkube, F. Takahashi, and M. Kato Tetrahedron Lett. 45 2004 2843
26. R. Labia, and C. Morin Chem. Lett. 1984 1007
27. G. Stork, and K. Zhao Tetrahedron Lett. 30 1989 2173
28. B. Dominguez, Y. Pazos, and A.R. de Lera J. Org. Chem. 65 2000 5917
29. (a) D.J. Hart, and D.-C. Ha Chem. Rev. 89 1989 1447
30. (b) D.J. Hart, K. Kanai, D.G. Thomas, and T.K. Yang J. Org. Chem. 48 1983 289
31. D. Amans, L. Barelle, V. Bellosta, and J. Cossy J. Org. Chem. 74 2009 7665
32. (a) M. Braun, and R. Devant Tetrahedron Lett. 25 1984 5031
33. (b) M. Braun Angew. Chem., Int. Ed. Engl. 26 1987 24
34. (c) M. Braun, and D. Waldmuller Synthesis 1989 856
35. M.E. Jung, and L.A. Light Tetrahedron Lett. 23 1982 3851
36. C. Palomo, J.M. Aizpurua, C. Cuevas, A. Mielgo, and R. Galarza Tetrahedron Lett. 36 1995 9027
37. S. Saito, T. Hasegawa, M. Inaba, R. Nishida, T. Fujii, S. Nomizu, and T. Moriwake Chem. Lett. 1984 1389
38. (a) G. Fráter Helv. Chim. Acta 62 1979 2825
39. (b) G. Fráter Helv. Chim. Acta 62 1979 2829
40. S.V. Ley, J. Norman, W.P. Griffith, and S.P. Marsden Synthesis 1994 639
41. J.M. Chong, H.E. Morton, and E. Piers Tetrahedron 45 1989 363
42. (a) C.A. Townsend, and L.T. Nguyen J. Am. Chem. Soc. 103 1981 4582
43. (b) C.A. Townsend, and L.T. Nguyen Tetrahedron Lett. 23 1982 4859
44. T.N. Saltzmann, R.W. Ratcliffe, B.G. Christensen, and F.A. Bouffard J. Am. Chem. Soc. 102 1980 6161
45. T. Jyojima, N. Miyamoto, M. Katohno, M. Nakata, S. Matsumura, and K. Toshia Tetrahedron Lett. 39 1998 6007
46. Interestingly, preliminary studies indicated that when the 1′-hydroxyl group was unprotected, selective desilylation of a 3′,11'-bis-tert-butyldimethylsilyl ether took place at the 3′-position.
47. (a) K. Carr, N.A. Greener, K.B. Mullah, F.M. Somerville, and J.K. Sutherland J. Chem. Soc., Perkin Trans. I 15 1992 1975
48. (b) S. Hanessian, and H.H. Khai Tetrahedron Lett. 40 1999 671
49. P. Quayle, J. Wang, J. Xu, and C.J. Urch Tetrahedron Lett. 39 1998 485
50. C.R. Johnson, and J.F. Kadow J. Org. Chem. 52 1987 1493