SmI2-induced reductive cyclization of optically active β-alkoxyvinyl sulfoxides with aldehyde

Tetrahedron Letters

Volumn 48, Issue 52, 2007, Pages 9171-9175

  Kimura, Tomohiro ^a   Hagiwara, Mayumi ^a   Nakata, Tadashi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

C C bond formation; Ethynyl p tolylsulfoxide; Polycyclic ethers; Samarium diiodide; Tetrahydropyranol

Indexed keywords

ALDEHYDE; BETA ALKOXYVINYL SULFOXIDE DERIVATIVE; SAMARIUM DIIODIDE; SULFOXIDE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 36448929785     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.102     Document Type: Article

References (48)

1. For reviews on polycyclic ethers, see:. Yasumoto T., and Murata M. Chem. Rev. 93 (1993) 1897
2. Shimizu Y. Chem. Rev. 93 (1993) 1685
3. Murata M., and Yasumoto T. Nat. Prod. Rep. 17 (2000) 293
4. Yasumoto T. Chem. Rec. 1 (2001) 228
5. Deranas A.H., Norte M., and Fernández J.J. Toxicon 39 (2001) 1101
6. For reviews on synthetic methods and total syntheses, see:. Alvarez E., Candenas M.-L., Pérez R., Ravelo J., and Martín J.D. Chem. Rev. 95 (1995) 1953
7. Fujiwara K., Hayashi N., Tokiwano T., and Murai A. Heterocycles 50 (1999) 561
8. Mori Y. Chem. Eur. J. 3 (1997) 849
9. Marmsäter F.P., and West F.G. Chem. Eur. J. 8 (2002) 4347
10. Inoue M. Org. Biomol. Chem. 2 (2004) 1811
11. Fujiwara K., and Murai A. Bull. Chem. Soc. Jpn. 77 (2004) 2129
12. Sasaki M., and Fuwa H. Synlett 2 (2004) 1811
13. Kadota I., and Yamamoto Y. Acc. Chem. Res. 38 (2005) 423
14. Inoue M. Chem. Rev. 105 (2005) 4379
15. Nakata T. Chem. Rev. 105 (2005) 4314
16. Clark J.S. Chem. Commun. (2006) 3571
17. Hori N., Matsukura H., Matsuo G., and Nakata T. Tetrahedron Lett. 40 (1999) 2811
18. Hori N., Matsukura H., and Nakata T. Org. Lett. 1 (1999) 1099
19. Matsuo G., Hori N., and Nakata T. Tetrahedron Lett. 40 (1999) 8859
20. Suzuki K., Matsukura H., Matsuo G., Koshino H., and Nakata T. Tetrahedron Lett. 43 (2002) 8653
21. Matsuo G., Kadohama H., and Nakata T. Chem. Lett. (2002) 148
22. Hori N., Matsuo G., Matsukura H., and Nakata T. Tetrahedron 58 (2002) 1853
23. Selected papers. Sato K., and Sasaki M. Angew. Chem., Int. Ed. 46 (2007) 2518
24. Fuwa H., Ebine M., Bourdelais A.J., Baden D.G., and Sasaki M. J. Am. Chem. Soc. 128 (2006) 16989
25. Fuwa H., Kakinuma N., Tachibana K., and Sasaki M. J. Am. Chem. Soc. 124 (2002) 14983
26. Kadota I., Takamura H., Sato K., Ohno A., Matsuda K., Satake M., and Yamamoto Y. J. Am. Chem. Soc. 125 (2003) 11893
27. Nagumo Y., Oguri H., Shindo Y., Sasaki S., Oishi T., Hirama M., Tomioka Y., Mizugaki M., and Tsumuraya T. Bioorg. Med. Chem. Lett. 11 (2001) 2037
28. Matsuo G., Kawamura K., Hori N., Matsukura H., and Nakata T. J. Am. Chem. Soc. 126 (2004) 14374
29. Takahashi S., Kubota A., and Nakata T. Angew. Chem., Int. Ed. 41 (2002) 4751
30. Kimura T., and Nakata T. Tetrahedron Lett. 48 (2007) 43
31. Jung J.H., Kim Y.W., Kim M.A., Choi S.Y., Chung Y.K., Kim T.-R., Shin S., and Lee E. Org. Lett. 9 (2007) 3225
32. Kimura, T.; Nakata, T. Abstract of Papers, Part 2, p 1203, 87th Annual Meeting of the Chemical Society of Japan, Osaka, Japan, March 25-28, 2007.
33. Kimura, T.; Hagiwara, M.; Nakata, T. Abstract of Papers, Part 4, p 20, 127th Annual Meeting of the Pharmaceutical Society of Japan, Toyama, Japan, March 28-30, 2007.
34. Kosugi H., Kitaoka M., Tagami K., Takahashi A., and Uda H. J. Org. Chem. 52 (1987) 1078
35. Solladie G., Hutt J., and Girardin A. Synthesis (1987) 173
36. Keum G., Kang S.B., Kim Y., and Lee E. Org. Lett. 6 (2004) 1895
37. Namy J.L., Girard P., and Kagan H.B. Nouv. J. Chim. 1 (1977) 5
38. Girard P., Namy J.L., and Kagan H.B. J. Am. Chem. Soc. 102 (1980) 2693
39. Kagan B.H. New J. Chem. 14 (1990) 453
40. 1/2 = 7.0 Hz, 1H). NOEs between C2-H and C6-H in 9b and 12b were observed.
41. Edmons D.J., Muir K.W., and Procter D.J. J. Org. Chem. 68 (2003) 3190
42. 1H NMR data. 10b: δ 6.53 (dd, J = 15.3, 5.5 Hz, 1H), 6.38 (dd, J = 15.3, 1.2 Hz, 1H), 5.67 (m, 1H), 4.69 (ddd, J = 11.0, 9.8, 4.9 Hz, 1H); 13b: δ 6.49 (dd, J = 15.2, 5.8 Hz, 1H), 6.41 (d, J = 15.2 Hz, 1H), 5.65 (m, 1H), 4.66 (ddd, J = 10.9, 10.9, 4.8 Hz, 1H). Alkaline hydrolysis of the diacetate 10b followed by acetylation afforded a 2:3 mixture of 2,6-syn-2,3-cis-tetrahydropyran 9b and 2,6-anti-2,3-trans-isomer via an intramolecular cyclization, and the same reaction of 13b predominantly afforded 2,6-anti-2,3-trans-tetrahydropyran. These results confirmed the β-configuration of the 3-acetoxy group in 10b and 13b.
43. 6 They proposed similar transition states through sulfoxide and Sm(III) coordination to those shown here. However, they noted that it is difficult to propose a transition state structure for conversion of 21 to 22; a possible transition state structure xii does not adopt the familiar chair-like conformation. Their result would be well explained by our proposed transition state, i.e., the cyclization of 21 should proceed through the transition state xiii to give 22.{A figure is presented}
44. 2O, 60 °C, 88% for 16, 79% for 19.
45. Synthesis of (+)-enantiomers of 18a and 18b from tri-O-acetyl-d-glucal:. Nicolaou K.C., Hwang C.-K., Marron B.E., DeFrees S.A., Couladouros E.A., Abe Y., Carrol P.J., and Snyder J.P. J. Am. Chem. Soc. 112 (1990) 3040
46. Shull B.K., Wu Z., and Koreeda M. J. Carbohyd. Chem. 15 (1996) 955
47. Matsuo G., Hinou H., Koshino H., Suenaga T., and Nakata T. Tetrahedron Lett. 41 (2000) 903
48. Köhnert S.M., and Maier M.E. Org. Lett. 4 (2002) 643