Brønsted acid-promoted azide-olefin [3 + 2] cyclo-additions for the preparation of contiguous amino-polyols: The importance of disiloxane ring size to a diastereoselective, bidirectional approach to zwittermicin A

Beilstein Journal of Organic Chemistry

Volumn 6, Issue , 2010, Pages 1206-1210

  Muchalski, Hubert ^a   Hong, Ki Bum ^a   Johnston, Jeffrey N ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Azide; Bidirectional synthesis; Cycloaddition; Dialkoxydisiloxane; TIPDS; Triazoline; Triflic acid; Zwittermicin A

Indexed keywords

EID: 78751547170     PISSN: 18605397     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.6.138     Document Type: Article

References (26)

1. Ogawa, T.; Katano, K.; Matsui, M. Tetrahedron 1980, 36, 2727-2733. doi:10.1016/0040-4020(80)80148-7
2. He, H.; Silo-Suh, L. A.; Handelsman, J.; Clardy, J. Tetrahedron Lett. 1994, 35, 2499-2502. doi:10.1016/S0040-4039(00)77154-1
3. Bodkin, J. A.; McLeod, M. D. J. Chem. Soc., Perkin Trans. 1 2002, 2733-2746. doi:10.1039/B111276G
4. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547. doi:10.1021/cr00032a009
5. Troyer, T. L.; Muchalski, H.; Johnston, J. N. Chem. Commun. 2009, 6195-6197. doi:10.1039/b913785h
6. Mahoney, J. M.; Smith, C. R.; Johnston, J. N. J. Am. Chem. Soc. 2005, 127, 1354-1355. doi:10.1021/ja045608c
7. Hong, K. B.; Donahue, M. G.; Johnston, J. N. J. Am. Chem. Soc. 2008, 130, 2323-2328. doi:10.1021/ja0779452
8. Donahue, M. G.; Hong, K. B.; Johnston, J. N. Bioorg. Med. Chem. Lett. 2009, 19, 4971-4973. doi:10.1016/j.bmcl.2009.07.067
9. Rogers, E. W.; Molinski, T. F. Org. Lett. 2007, 9, 437-440. doi:10.1021/ol062804a
10. Rogers, E.; Dalisay, D.; Molinski, T. Angew. Chem., Int. Ed. 2008, 47, 8086-8089. doi:10.1002/anie.200801561
11. Rogers, E. W.; Molinski, T. F. J. Org. Chem. 2009, 74, 7660-7664. doi:10.1021/jo901007v
12. Rogers, E. W.; Dalisay, D. S.; Molinski, T. F. Bioorg. Med. Chem. Lett. 2010, 20, 2183-2185. doi:10.1016/j.bmcl.2010.02.032
13. Magnuson, S. Tetrahedron 1995, 51, 2167-2213. doi:10.1016/0040-4020(94) 01070-G
14. Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9-17. doi:10.1021/ar00037a002
15. Norris, P.; Horton, D.; Giridhar, D. E. Tetrahedron Lett. 1996, 37, 3925-3928. doi:10.1016/0040-4039(96)00716-2
16. Herdeis, C.; Schiffer, T. Synthesis 1997, 1405-1410. doi:10.1055/s-1997- 1366
17. Krülle, T. M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. doi:10.1016/S0957-4166(97)00561-2
18. Herdeis, C.; Schiffer, T. Tetrahedron 1999, 55, 1043-1056. doi:10.1016/S0040-4020(98)01085-0
19. Broggini, G.; Garanti, L.; Molteni, G.; Pilati, T. Tetrahedron: Asymmetry 2001, 12, 1201-1206. doi:10.1016/S0957-4166(01)00190-2
20. Broggini, G.; Marchi, I. D.; Martinelli, M.; Paladino, G.; Penoni, A. Lett. Org. Chem. 2004, 1, 221-223. doi:10.2174/1570178043400956
21. Chen, M.; Gan, Y.; Harwood, L. M. Synlett 2008, 2008, 2119-2121. doi:10.1055/s-2008-1078595
22. Reddy, D. S.; Judd, W. R.; Aubé, J. Org. Lett. 2003, 5, 3899-3902. doi:10.1021/ol0355130
23. Corey, E. J.; Hopkins, P. B. Tetrahedron Lett. 1982, 23, 4871-4874. doi:10.1016/S0040-4039(00)85735-4
24. Kocienski, P. Protecting groups; Georg Thieme: New York, 2004.
25. Wuts, P. Greene's protective groups in organic synthesis; Wiley-Interscience: Hoboken, N.Y., 2007.
26. Caution should always be exercised when azides are heated or treated with strong acid, but we have never observed an uncontrolled reaction or off-gas during our studies.