Construction of cyclopentanol derivatives via three-component coupling of silyl glyoxylates, acetylides, and nitroalkenes

Organic Letters

Volumn 14, Issue 2, 2012, Pages 652-655

  Boyce, Gregory R ^a   Liu, Shubin ^b   Johnson, Jeffrey S ^a  

^a University of North Carolina at Chapel Hill   (United States)

^b UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALKENE; CYCLOPENTANE DERIVATIVE; CYCLOPENTANOL; GLYOXYLIC ACID DERIVATIVE; NITRO DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HYDROXYLATION; STEREOISOMERISM;

ACETYLENE; ALKENES; CYCLIZATION; CYCLOPENTANES; GLYOXYLATES; HYDROXYLATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITRO COMPOUNDS; STEREOISOMERISM;

EID: 84862909347     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2033527     Document Type: Article

References (43)

1. Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779-844
2. Flatt, P.; Mahmud, T. Nat. Prod. Rep. 2007, 24, 358-392
3. Kurteva, V. B.; Afonso, C. A. M. Chem. Rev. 2009, 109, 6809-6857
4. Murao, S.; Sakai, T.; Gibo, H.; Nakayama, T.; Shin, T. Agric. Biol. Chem. 1991, 55, 895-897
5. Ohkuma, Y.; Kinoshita, R.; Enokita, R. J. Antibiot. 1991, 44, 1165-1168
6. Wiley, P. F.; Jahnke, H. K.; MacKellar, F.; Kelly, R. B.; Argoudelis, A. D. J. Org. Chem. 1970, 35, 1420-1425
7. Sutko, J. L.; Airey, J. A.; Welch, W.; Ruest, L. Pharmacol. Rev. 1997, 49, 53-98
8. Umino, K.; Furama, T.; Matzuzawa, N.; Awataguchi, Y.; Ito, Y.; Okuda, T. J. Antibiot. 1973, 26, 506-512
9. Umino, K.; Takeda, N.; Ito, Y.; Okuda, T. Chem. Pharm. Bull. 1974, 22, 1233-1238
10. Choi, J.; Lee, K.-T.; Choi, M.-Y.; Nam, J.-H.; Jung, H.-J.; Park, S.-K.; Park, H.-J. Biol. Pharm. Bull. 2005, 28, 1915-1918
11. Kuwajima, I.; Kato, M. Tetrahedron Lett. 1980, 21, 623-626
12. Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423-1424
13. Nicewicz, D. A.; Brétéché, G.; Johnson, J. S. Org. Synth. 2008, 85, 278-286
14. Nicewicz, D. A.; Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 6170-6171
15. Greszler, S. N.; Johnson, J. S. Angew. Chem., Int. Ed. 2009, 48, 3689-3691
16. Schmitt, D. C.; Johnson, J. S. Org. Lett. 2010, 12, 944-947
17. Boyce, G. R.; Johnson, J. S. Angew. Chem., Int. Ed. 2010, 49, 8930-8933
18. Yao, M.; Lu, C.-D. Org. Lett. 2011, 13, 2782-2785
19. Krause, N.; Stephen, A.; Hashmi, K. Modern Allene Chemistry; Wiley-VCH: Weinheim, 2005.
20. Kato, M.; Kuwajima, I. Bull. Chem. Soc. Jpn. 1984, 57, 827-830
21. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-7800
22. Tius, M. A.; Hu, H. Tetrahedron Lett. 1998, 39, 5937-5940
23. Yoshizawa, K.; Shioiri, T. Tetrahedron Lett. 2006, 47, 757-761
24. Reynolds, T. E.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 7806-7809
25. Brekan, J. A.; Reynolds, T. E.; Scheidt, K. A. J. Am. Chem. Soc. 2010, 132, 1472-1473
26. Sasaki, M.; Kondo, Y.; Kawahata, M.; Yamaguchi, K.; Takeda, K. Angew. Chem., Int. Ed. 2011, 50, 6375-6378
27. Mitachi, K.; Yamamoto, T.; Kondo, F.; Shimizu, T.; Miyashita, M.; Tanino, K. Chem. Lett. 2010, 39, 630-632
28. Iida, K.-I.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310-10311
29. Nakamura, E.; Aoki, S.; Sekiya, K.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056-8066
30. Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84
31. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302
32. CCDC 827440 (5a-TIPS) and CCDC 830724 (8a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
33. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
34. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
35. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222
36. Francl, M. M.; Pietro, W. J.; Henre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654-3665
37. Casiraghi, G.; Battistini, L.; Curti, C.; Rassu, G.; Zanardi, F. Chem. Rev. 2011, 111, 3076-3154
38. Lecea, B.; Arrieta, A.; Morao, I.; Cossío, F. P. Chem.-Eur. J. 1997, 3, 20-28
39. Hara, K.; Tosaki, S.-Y.; Gnanadesikan, V.; Morimoto, H.; Harada, S.; Sugita, M.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Tetrahedron 2009, 65, 5030-5036
40. Ziegler, F. E.; Chakraborty, U. R.; Wester, R. T. Tetrahedron Lett. 1982, 23, 3237-3240
41. Luzzio, F. A. Tetrahedron 2001, 57, 915-945
42. Plietker, B. J. Org. Chem. 2004, 69, 8287-8296
43. Donohoe, T. J.; Blades, K.; Moore, P. R.; Waring, M. J.; Winter, J. J. G.; Helliwell, M.; Newcombe, N. J.; Stemp, G. J. Org. Chem. 2002, 67, 7946-7956