Effective combination of two-directional synthesis and rhenium(VII) chemistry: Total synthesis of meso polyether teurilene

Journal of the American Chemical Society

Volumn 121, Issue 29, 1999, Pages 6792-6797

  Morimoto, Yoshiki ^a   Iwai, Toshiyuki ^a   Kinoshita, Takamasa ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; POLYETHER DERIVATIVE; RHENIUM; TETRAHYDROFURAN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033612739     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990154i     Document Type: Article

References (48)

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18. For the previous total synthesis of teurilene (1), see the following: (a) Hashimoto, M.; Yanagiya, M.; Shirahama, H. Chem. Lett. 1988, 645- 646. (b) Hashimoto, M.; Harigaya, H.; Yanagiya, M.; Shirahama, H. Tetrahedron Lett. 1988, 29, 5947-5948. (c) Hashimoto, M.; Harigaya, H.; Yanagiya, M.; Shirahama, H. J. Org. Chem. 1991, 56, 2299-2311. For synthetic approaches toward 1, see the following: (d) Hoye, T. R.; Suhadolnik, J. C. Tetrahedron 1986, 42, 2855-2862. (e) Hoye, T. R.; Jenkins, S. A. J. Am. Chem. Soc. 1987, 109, 6196-6198. (f) Lindel, T.; Franck, B. Tetrahedron Lett. 1995, 36, 9465-9468.
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34. For application of this Re(VII) protocol to natural products synthesis, see the following: (a) Sinha, S. C.; Sinha-Bagchi, A.; Keinan, E. J. Am. Chem. Soc. 1995, 117, 1447-1448. (b) Sinha, S. C.; Sinha-Bagchi, A.; Yazbak, A.; Keinan, E. Tetrahedron Lett. 1995, 36, 9257-9260. (c) Sinha, S. C.; Sinha, A.; Yazbak, A.; Keinan, E. J. Org. Chem. 1996, 61, 7640- 7641. (d) Keinan, E.; Sinha, A.; Yazbak, A.; Sinha, S. C.; Sinha, S. C. Pure Appl. Chem. 1997, 69, 423-430. (e) McDonald, F. E.; Schultz, C. C. Tetrahedron 1997, 53, 16435-16448. (f) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1997, 119, 12014-12015. (g) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017- 4018.
35. For application of this Re(VII) protocol to natural products synthesis, see the following: (a) Sinha, S. C.; Sinha-Bagchi, A.; Keinan, E. J. Am. Chem. Soc. 1995, 117, 1447-1448. (b) Sinha, S. C.; Sinha-Bagchi, A.; Yazbak, A.; Keinan, E. Tetrahedron Lett. 1995, 36, 9257-9260. (c) Sinha, S. C.; Sinha, A.; Yazbak, A.; Keinan, E. J. Org. Chem. 1996, 61, 7640-7641. (d) Keinan, E.; Sinha, A.; Yazbak, A.; Sinha, S. C.; Sinha, S. C. Pure Appl. Chem. 1997, 69, 423-430. (e) McDonald, F. E.; Schultz, C. C. Tetrahedron 1997, 53, 16435-16448. (f) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1997, 119, 12014-12015. (g) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017- 4018.
36. For application of this Re(VII) protocol to natural products synthesis, see the following: (a) Sinha, S. C.; Sinha-Bagchi, A.; Keinan, E. J. Am. Chem. Soc. 1995, 117, 1447-1448. (b) Sinha, S. C.; Sinha-Bagchi, A.; Yazbak, A.; Keinan, E. Tetrahedron Lett. 1995, 36, 9257-9260. (c) Sinha, S. C.; Sinha, A.; Yazbak, A.; Keinan, E. J. Org. Chem. 1996, 61, 7640- 7641. (d) Keinan, E.; Sinha, A.; Yazbak, A.; Sinha, S. C.; Sinha, S. C. Pure Appl. Chem. 1997, 69, 423-430. (e) McDonald, F. E.; Schultz, C. C. Tetrahedron 1997, 53, 16435-16448. (f) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1997, 119, 12014-12015. (g) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017- 4018.
37. For application of this Re(VII) protocol to natural products synthesis, see the following: (a) Sinha, S. C.; Sinha-Bagchi, A.; Keinan, E. J. Am. Chem. Soc. 1995, 117, 1447-1448. (b) Sinha, S. C.; Sinha-Bagchi, A.; Yazbak, A.; Keinan, E. Tetrahedron Lett. 1995, 36, 9257-9260. (c) Sinha, S. C.; Sinha, A.; Yazbak, A.; Keinan, E. J. Org. Chem. 1996, 61, 7640- 7641. (d) Keinan, E.; Sinha, A.; Yazbak, A.; Sinha, S. C.; Sinha, S. C. Pure Appl. Chem. 1997, 69, 423-430. (e) McDonald, F. E.; Schultz, C. C. Tetrahedron 1997, 53, 16435-16448. (f) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1997, 119, 12014-12015. (g) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017- 4018.
38. For application of this Re(VII) protocol to natural products synthesis, see the following: (a) Sinha, S. C.; Sinha-Bagchi, A.; Keinan, E. J. Am. Chem. Soc. 1995, 117, 1447-1448. (b) Sinha, S. C.; Sinha-Bagchi, A.; Yazbak, A.; Keinan, E. Tetrahedron Lett. 1995, 36, 9257-9260. (c) Sinha, S. C.; Sinha, A.; Yazbak, A.; Keinan, E. J. Org. Chem. 1996, 61, 7640- 7641. (d) Keinan, E.; Sinha, A.; Yazbak, A.; Sinha, S. C.; Sinha, S. C. Pure Appl. Chem. 1997, 69, 423-430. (e) McDonald, F. E.; Schultz, C. C. Tetrahedron 1997, 53, 16435-16448. (f) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1997, 119, 12014-12015. (g) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017- 4018.
39. For application of this Re(VII) protocol to natural products synthesis, see the following: (a) Sinha, S. C.; Sinha-Bagchi, A.; Keinan, E. J. Am. Chem. Soc. 1995, 117, 1447-1448. (b) Sinha, S. C.; Sinha-Bagchi, A.; Yazbak, A.; Keinan, E. Tetrahedron Lett. 1995, 36, 9257-9260. (c) Sinha, S. C.; Sinha, A.; Yazbak, A.; Keinan, E. J. Org. Chem. 1996, 61, 7640- 7641. (d) Keinan, E.; Sinha, A.; Yazbak, A.; Sinha, S. C.; Sinha, S. C. Pure Appl. Chem. 1997, 69, 423-430. (e) McDonald, F. E.; Schultz, C. C. Tetrahedron 1997, 53, 16435-16448. (f) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1997, 119, 12014-12015. (g) Sinha, S. C.; Sinha, A.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 4017-4018.
40. Morimoto, Y.; Iwai, T. J. Am. Chem. Soc. 1998, 120, 1633-1634.
41. D -20.0 (c 2.54, MeOH).
42. 13C NMR, IR, MS, and HRMS spectra. See the Experimental Section.
43. 3P, THF, rt, 2 h).
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46. The residual optical rotation of synthetic 1 is an experimental error, and neither 3 nor 9 shows a rotation.
47. This chelation effect on the neighboring THF ring has also been observed in secondary alcohols (refs 10g and 1 If).
48. More recently, Sinha et al. have reported rules of stereoselectivity in tandem oxidative polycyclization reaction of bishomoallylic secondary alcohols with rhemum(VII) oxides. See the following: Sinha, S. C.; Keinan, E.; Sinha, S. C. J. Am. Chem. Soc. 1998, 120, 9076-9077.