A simple and general platform for generating stereochemically complex polyene frameworks by iterative cross-coupling

Angewandte Chemie - International Edition

Volumn 49, Issue 47, 2010, Pages 8860-8863

  Lee, Suk Joong ^a   Anderson, Thomas M ^a   Burke, Martin D ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

haloboronic acids; iterative cross coupling; MIDA boronates; polyenes; vacidin A

Indexed keywords

HALOBORONIC ACIDS; ITERATIVE CROSS-COUPLING; MIDA BORONATES; POLYENES; VACIDIN A;

ACIDS; CHEMICAL REACTIONS;

ORGANIC COMPOUNDS;

BORONIC ACID DERIVATIVE; CANDICIDIN; DRUG DERIVATIVE; HALOGEN; IMINO ACID; N METHYLDIGLYCINE; N-METHYLIMINODIACETIC ACID; POLYENE; VACIDIN A;

ARTICLE; CHEMISTRY; STEREOISOMERISM;

BORONIC ACIDS; CANDICIDIN; HALOGENS; IMINO ACIDS; POLYENES; STEREOISOMERISM;

EID: 78449258277     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201004911     Document Type: Article

References (53)

1. For recent reviews on iterative cross-coupling, see
2. C. Wang, F. Glorius, Angew. Chem. 2009, 121, 5342 - 5346
3. Angew. Chem. Int. Ed. 2009, 48, 5240 - 5244
4. M. Tobisu, N. Chatani, Angew. Chem. 2009, 121, 3617 - 3620
5. Angew. Chem. Int. Ed. 2009, 48, 3565 - 3568
6. Angew. Chem. 2009, 121, 3617 - 3620; for an alternative iterative cross-coupling system based on 1,8-diaminonaphthalene, see
7. H. Noguchi, K. Hojo, M. Suginome, J. Am. Chem. Soc. 2007, 129, 758 - 759
8. H. Noguchi, T. Shioda, C.-M. Chou, M. Suginome, Org. Lett. 2008, 10, 377 - 380.
9. E. P. Gillis, M. D. Burke, J. Am. Chem. Soc. 2007, 129, 6716 - 6717
10. S. J. Lee, K. C. Gray, J. S. Paek, M. D. Burke, J. Am. Chem. Soc. 2008, 130, 466 - 468
11. E. P. Gillis, M. D. Burke, J. Am. Chem. Soc. 2008, 130, 14084 - 14085
12. D. M. Knapp, E. P. Gillis, M. D. Burke, J. Am. Chem. Soc. 2009, 131, 6961 - 6963
13. E. M. Woerly, A. H. Cherney, E. K. Davis, M. D. Burke, J. Am. Chem. Soc. 2010, 132, 6941 - 6943
14. G. D. Dick, D. M. Knapp, E. P. Gillis, M. D. Burke, Org. Lett. 2010, 12, 2314 - 2317
15. E. P. Gillis, M. D. Burke, Aldrichimica Acta 2009, 42, 17 - 27
16. many MIDA boronates, including 6 (Sigma-Aldrich: 700231), are now commercially available.
17. For a recent review on cross-coupling-based syntheses of polyene natural product frameworks, see:, E. Negishi, G. Wang, H. Rao, Z. Wu, J. Org. Chem. 2010, 75, 3151 - 3182.
18. For some additional additional selected examples of bifunctional building blocks for polyene synthesis, see
19. E. J. Corey, R. H. Wollenberg, J. Org. Chem. 1975, 40, 3788 - 3789
20. S. Hyuga, Y. Chiba, N. Yamashina, S. Hara, A. Suzuki, Chem. Lett. 1987, 1757 - 1760
21. S. K. Stewart, A. Whiting, Tetrahedron Lett. 1995, 36, 3925 - 3928
22. F. Lhermitte, B. Carboni, Synlett 1996, 377 - 379
23. B. H. Lipshutz, C. Lindsley, J. Am. Chem. Soc. 1997, 119, 4555 - 4556
24. T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2000, 611, 392 - 402
25. S. E. Denmark, S. A. Tymonko, J. Am. Chem. Soc. 2005, 127, 8004 - 8005
26. R. S. Coleman, X. Lu, I. Modolo, J. Am. Chem. Soc. 2007, 129, 3826 - 3827.
27. For the development of an iterative cross-coupling-enabling 3,3-dialkyltriazene masking group for aryl iodides, see
28. J. S. Moore, E. J. Weinstein, Z. Wu, Tetrahedron Lett. 1991, 32, 2465 - 2466
29. J. Zhang, J. S. Moore, Z. Xu, R. A. Aguirre, J. Am. Chem. Soc. 1992, 114, 2273 - 2274.
30. F. David-Quillot, J. Thibonnet, D. Marsacq, M. Abarbri, A. Duchne, Tetrahedron Lett. 2000, 41, 9981 - 9984.
31. H. Oda, Y. Morizawa, K. Oshima, H. Nozaki, Tetrahedron Lett. 1984, 25, 3221 - 3224
32. T. Schwier, V. Gevorgyan, Org. Lett. 2005, 7, 5191 - 5194.
33. T. H. Chan, P. W. K. Lau, W. Mychajlowskij, Tetrahedron Lett. 1977, 18, 3317 - 3320
34. D. P. Stamos, A. G. Taylor, Y. Kishi, Tetrahedron Lett. 1996, 37, 8647 - 8650
35. E. A. Ilardi, C. E. Stivala, A. Zakarian, Org. Lett. 2008, 10, 1727 - 1730.
36. D. S. Matteson, K. Peacock, J. Am. Chem. Soc. 1960, 82, 5759 - 5760.
37. J. R. Struble, S. J. Lee, M. D. Burke, Tetrahedron 2010, 66, 4710 - 4718.
38. E. J. Corey, P. Ulrich, J. M. Fitzpatrick, J. Am. Chem. Soc. 1976, 98, 222 - 224
39. hydrostannylations of alkynylboranes:, N. Guennouni, F. Lhermitte, S. Cochard, B. Carboni, Tetrahedron 1995, 51, 6999 - 7018.
40. H. Hofmeister, K. Annen, H. Laurent, R. Wiechert, Angew. Chem. 1984, 96, 720 - 722
41. Angew. Chem. Int. Ed. Engl. 1984, 23, 727 - 729.
42. D. J. Pasto, R. T. Taylor, Org. React. 1991, 40, 91 - 107.
43. E. Lukevics, P. Arsenyan, M. Fleisher, J. Popelis, O. Pudova, Main Group Met. Chem. 1999, 22, 655 - 660.
44. E. Piers, R. T. Skerlj, J. Chem. Soc. Chem. Commun. 1987, 1025 - 1026
45. T. Nakano, Y. Senda, T. Miyamoto, Chem. Lett. 2000, 1408 - 1409.
46. M. Murakami, T. Matsuda, K. Itami, S. Ashida, M. Terayama, Synthesis 2004, 1522 - 1526.
47. G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1996, 118, 2748 - 2749.
48. R. Martin, S. L. Buchwald, Acc. Chem. Res. 2008, 41, 1461.
49. Generally, no alternative stereoisomers were observed by NMR spectroscopy of the crude products. Polyene 20 partially isomerized upon concentration (see Supporting Information).
50. S. Igarashi, K. Ogata, A. Miyake, Jpn. J. Antibiot. Ser. B 1956, 9, 79 - 80
51. P. Sowiski, P. Gariboldi, A. Czerwiski, E. Borowski, J. Antibiot. 1989, 42, 1631 - 1638.
52. 24 was also prepared using the metal-selective coupling/iododegermylation strategy; see Supporting Information for details.
53. The indicated configuration of the polyene motif in 25 is consistent with an extensive series of multidimensional NMR studies (see Supporting Information for details).