Selective deprotection of silyl ethers with sodium periodate

Synthesis

Volumn , Issue 11, 2009, Pages 1904-1908

  Li, Jun ^a   Menche, Dirk ^b  

^a HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Natural products; Selective deprotection; Silyl ethers; Sodium periodate; Synthetic methodology

Indexed keywords

NATURAL PRODUCTS; SELECTIVE DEPROTECTION; SILYL ETHERS; SODIUM PERIODATE; SYNTHETIC METHODOLOGY;

ORGANIC COMPOUNDS; SILANES; SODIUM;

ETHERS;

PERIODATE SODIUM; SILANE DERIVATIVE; TETRAHYDROFURAN; WATER;

ARTICLE; DEPROTECTION REACTION; REACTION ANALYSIS;

EID: 67650045451     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1088062     Document Type: Article

References (35)

1. Jarowicki, K.; Kocienski, P. J. Chem. Soc., Perkin Trans. 1 2000, 2495.
2. Green, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999.
3. Kocienski, P. Protecting Groups; Thieme: Stuttgart, 1994.
4. Nelson, T. D.; Crouch, R. D. Synthesis 1996, 1031.
5. Crouch, R. D. Tetrahedron 2004, 60, 5833.
6. For a review, see: Muzart, J. Synthesis 1993, 11.
7. (a) Tanemura, K.; Suzuki, T.; Horaguchi, T. J. Chem. Soc., Perkin Trans. 1 1992, 2997.
8. (b) Vaino, A. R.; Szarek, W. A. Chem. Commun. 1996, 2351.
9. (c) Paterson, I.; Cowden, C. J.; Rahn, V. S. Synlett 1998, 915.
10. (d) Wang, M.; Li, C.; Yin, D.; Liang, X.-T. Tetrahedron Lett. 2002, 43, 8727.
11. (e) Karimi, B.; Rajabi, J. Org. Lett. 2004, 6, 2841.
12. (f) Iranpoor, N.; Firouzabadi, H.; Pourali, A. R. Synth. Commun. 2005, 35, 1527.
13. (g) Raghuvanshi, R. S.; Singh, K. N. Synth. Commun. 2007, 37, 1371.
14. Ali, S. M.; Georg, G. I. Tetrahedron Lett. 1997, 38, 1703.
15. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557.
16. Shimano, K.; Ge, Y.; Sakaguchi, K.; Isoe, S. Tetrahedron Lett. 1996, 37, 2253.
17. Shahid, K. A.; Mursheda, J.; Okazaki, M.; Shuto, Y.; Goto, F.; Kiyooka, S. Tetrahedron Lett. 2002, 43, 6377.
18. Ichikawa, S.; Shuto, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1997, 62, 1368.
19. Pilli, R. A.; Victor, M. M. Tetrahedron Lett. 1998, 39, 4421.
20. Trauner, D.; Schwarz, J. B.; Danishefsky, S. J. Angew. Chem. Int. Ed. 1999, 38, 3542.
21. Chandrasekhar, S.; Mohanty, P. K.; Takhi, M. J. Org. Chem. 1997, 62, 2628.
22. Koeller, S.; Lellouche, J.-P. Tetrahedron Lett. 1999, 40, 7043.
23. Hwu, J. R.; Jain, M. L.; Tsai, F.-Y.; Tsay, S.-C.; Balakumar, A.; Hakimelahi, G. H. J. Org. Chem. 2000, 65, 5077.
24. Chen, M.-Y.; Lu, K.-C.; Lee, A. S.-Y.; Lin, C.-C. Tetrahedron Lett. 2002, 43, 2777.
25. Tandon, N.; Begley, T. P. Synth. Commun. 1997, 27, 2953.
26. For recent examples, see: (a) Clark, J. S.; Baxter, C. A.; Dossetter, A. G.; Poigny, S.; Castro, J. L.; Whittingham, W. G. J. Org. Chem. 2008, 73, 1040.
27. (b) Ferrie, L.; Boulard, L.; Pradaux, F.; Bouzbouz, S.; Reymond, S.; Capdevielle, P.; Cossy, J. J. Org. Chem. 2008, 73, 1864.
28. (c) Smith, A. B. III; Razler, T. M.; Meis, R. M.; Pettit, G. R. J. Org. Chem. 2008, 73, 1201.
29. Menche, D.; Arikan, F.; Perlova, O.; Horstmann, N.; Ahlbrecht, W.; Wenzel, S. C.; Jansen, R.; Irschik, H.; Müller, R. J. Am. Chem. Soc. 2008, 129, 14234.
30. Baker, R.; Castro, J. L. J. Chem. Soc., Perkin Trans. 1 1990, 47.
31. Gogoi, P.; Sarmah, G. K.; Konwar, D. J. Org. Chem. 2004, 69, 5153.
32. Yasuda, M.; Onishi, Y.; Ueba, M.; Miyai, T.; Baba, A. J. Org. Chem. 2001, 66, 7741.
33. White, J. D.; Carter, J. P.; Kezar, H. S. III J. Org. Chem. 1982, 47, 929.
34. Menche, D.; Hassfeld, J.; Li, J.; Rudolph, S. J. Am. Chem. Soc. 2007, 129, 6100.
35. Arikan, F.; Li, J.; Menche, D. Org. Lett. 2008, 10, 3521.