Formal synthesis of ent-dysiherbaine from sulfinyl dihydropyrans by sigmatropic rearrangement and tethered aminohydroxylation

Tetrahedron Letters

Volumn 48, Issue 46, 2007, Pages 8141-8144

  Fernández de la Pradilla, Roberto ^a   Lwoff, Nadia ^a   Viso, Alma ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Allylic sulfoxides; Sigmatropic rearrangement; Tethered aminohydroxylation

Indexed keywords

DYSIHERBAINE; PYRAN DERIVATIVE;

AMINOHYDROXYLATION; ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; STEREOSPECIFICITY;

EID: 35348848981     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.103     Document Type: Article

References (39)

1. Sakai R., Kamiya H., Murata M., and Shimamoto K. J. Am. Chem. Soc. 119 (1997) 4112-4116
2. Total syntheses:. Snider B.B., and Hawryluk N.A. Org. Lett. 2 (2000) 635-638
3. Sasaki M., Koike T., Sakai R., and Tachibana K. Tetrahedron Lett. 41 (2000) 3923-3926
4. Masaki H., Maeyama J., Kamada K., Esumi T., Iwabuchi Y., and Hatakeyama S. J. Am. Chem. Soc. 122 (2000) 5216-5217
5. Phillips D., and Chamberlin A.R. J. Org. Chem. 67 (2002) 3194-3201
6. Sasaki M., Akiyama N., Tsubone K., Shoji M., Oikawa M., and Sakai R. Tetrahedron Lett. 48 (2007) 5697-5700
7. Partial and formal syntheses:. Naito T., Nair J.S., Nishiki A., Yamashita K., and Kiguchi T. Heterocycles 53 (2000) 2611-2615
8. Miyata O., Iba R., Hashimoto J., and Naito T. Org. Biomol. Chem. 1 (2003) 772-774
9. Kang S.H., and Lee Y.M. Synlett (2003) 993-994
10. Huang J.-M., Xu K.-C., and Loh T.-P. Synthesis (2003) 755-764
11. Cohen J.L., and Chamberlin A.R. Tetrahedron Lett. 48 (2007) 2533-2536
12. Related studies:. Friestad G.K., and Mathies A.K. Tetrahedron 63 (2007) 9373-9381
13. Donohoe T.J., Johnson P.D., Cowley A., and Keenan M. J. Am. Chem. Soc. 124 (2002) 12934-12935
14. Donohoe T.J., Johnson P.D., Helliwell M., and Keenan M. Chem. Commun. (2001) 2078-2079
15. Donohoe T.J., Johnson P.D., and Pye R.J. Org. Biomol. Chem. 1 (2003) 2025-2028
16. Donohoe T.J., Johnson P.D., Pye R.J., and Keenan M. Org. Lett. 6 (2004) 2583-2585
17. Kenworthy M.N., McAllister G.D., and Taylor R.J.K. Tetrahedron Lett. 45 (2004) 6661-6664
18. Donohoe T.J., Johnson P.D., Pye R.J., and Keenan M. Org. Lett. 7 (2005) 1275-1277
19. Donohoe T.J., Chughtai M.J., Klauber D.J., Griffin D., and Campbell A.D. J. Am. Chem. Soc. 128 (2006) 2514-2515
20. Fernández de la Pradilla R., and Tortosa M. Org. Lett. 6 (2004) 2157-2160
21. Vedejs E., Engler D.A., and Telschow J.E. J. Org. Chem. 43 (1978) 188-196
22. Baudin J.-B., Julia M., and Rolando C. Tetrahedron Lett. 26 (1985) 2333-2334
23. Hwu J.R. J. Org. Chem. 48 (1983) 4432-4433
24. Chemla F., Julia M., and Uguen D. Bull. Soc. Chim. Fr. 130 (1993) 547-553
25. Hoppe D., Tebben P., Reggelin M., and Bolte M. Synthesis (1997) 183-189
26. Fujishima H., Takeshita H., Toyota M., and Ihara M. J. Org. Chem. 66 (2000) 2394-2399
27. For recent examples, see:. Brebion F., Nàjera F., Delouvrié B., Lacôte E., Fensterbank L., and Malacria M. Synthesis (2007) 2273-2278
28. Pelc M.J., and Zakarian A. Tetrahedron Lett. 47 (2006) 7519-7523
29. Satoh T., and Miyagawa T. Tetrahedron Lett. 47 (2006) 1981-1983
30. Evans D.A., Andrews G.C., and Sims C.L. J. Am. Chem. Soc. 93 (1971) 4956-4957
31. Evans D.A., and Andrews G.C. J. Am. Chem. Soc. 94 (1972) 3672-3674
32. Evans D.A., and Andrews G.C. Acc. Chem. Res. 7 (1974) 147-155
33. These results will be described in detail in a full account of this research.
34. Hughes D.L. Org. Prep. Proced. Int. 28 (1996) 127-164
35. Nadia Lwoff, MS Thesis, Universidad Complutense de Madrid, September 2005.
36. The tethered aminohydroxylation was carried out in small scale and it has been previously reported that under these conditions the yields vary unpredictably from 4% to 40%. See:. Curtis K.L., Fawcett J., and Handa S. Tetrahedron Lett. 46 (2005) 5297-5300
37. 2S with good yield and selectivity (90%, cis:trans, 91:9). Unfortunately, selective protection to generate 18 was not efficient. These results will be described in detail in due time.
38. We first studied the process for the tosyloxy derivative, but the yields were moderate and the starting material was not recovered, under these conditions. In contrast, the mesitylsulfonyloxy derivative was more stable and gave higher yields in the aminohydroxylation step.
39. Merten J., Hennig A., Schwab P., Fröhlich R., Tokalov S.V., Gutzeit H.O., and Metz P. Eur. J. Org. Chem. (2006) 1144-1161