Mitsunobu reactions with methanesulfonic acid; the replacement of equatorial hydroxyl groups by azide with net retention of configuration

Tetrahedron Letters

Volumn 38, Issue 24, 1997, Pages 4305-4308

  Davis, Anthony P ^a   Dresen, Stephan ^a   Lawless, Laurence J ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; CHOLIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030919027     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00886-1     Document Type: Article

References (22)

1. Mitsunobu, O. Synthesis 1981, 1. Hughes, D. L. Organic Reactions 1992, 42, 335. Jenkins, I. D.; Mitsunobu, O. Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, 1995, p 5379.
2. Mitsunobu, O. Synthesis 1981, 1. Hughes, D. L. Organic Reactions 1992, 42, 335. Jenkins, I. D.; Mitsunobu, O. Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, 1995, p 5379.
3. Mitsunobu, O. Synthesis 1981, 1. Hughes, D. L. Organic Reactions 1992, 42, 335. Jenkins, I. D.; Mitsunobu, O. Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, 1995, p 5379.
4. See e.g. Koppel, I.; Koppel, J.; Degerbeck, F.; Grehn, L.; Ragnarsson, U. J. Org. Chem. 1991, 56, 7172. Tsunoda, T.; Yamiyama, Y.; Ito, S. Tetrahedron Lett. 1993, 34, 1639. Bell, K. E.; Knight, D. W.; Gravestock, M. B. Tetrahedron Lett. 1995, 36, 8681.
5. See e.g. Koppel, I.; Koppel, J.; Degerbeck, F.; Grehn, L.; Ragnarsson, U. J. Org. Chem. 1991, 56, 7172. Tsunoda, T.; Yamiyama, Y.; Ito, S. Tetrahedron Lett. 1993, 34, 1639. Bell, K. E.; Knight, D. W.; Gravestock, M. B. Tetrahedron Lett. 1995, 36, 8681.
6. See e.g. Koppel, I.; Koppel, J.; Degerbeck, F.; Grehn, L.; Ragnarsson, U. J. Org. Chem. 1991, 56, 7172. Tsunoda, T.; Yamiyama, Y.; Ito, S. Tetrahedron Lett. 1993, 34, 1639. Bell, K. E.; Knight, D. W.; Gravestock, M. B. Tetrahedron Lett. 1995, 36, 8681.
7. Campbell, D. A. J. Org. Chem. 1992, 57, 6331. Campbell, D. A.; Bermak, J. C. J. Org. Chem. 1994, 59, 658.
8. Campbell, D. A. J. Org. Chem. 1992, 57, 6331. Campbell, D. A.; Bermak, J. C. J. Org. Chem. 1994, 59, 658.
9. Varasi, M.; Walker, K. A. M.; Maddox, M. L. J. Org. Chem. 1987, 52, 4235.
10. (a) Galynker, I.; Still, W. C. Tetrahedron Lett. 1982, 23, 4461.
11. (b) Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487.
12. Leading refs.: Davis, A. P. Chem. Soc. Rev. 1993, 22, 243. Davis, A. P.; Bonar-Law, R. P.; Sanders, J. K. M. Comprehensive Supramolecular Chemistry; Pergamon: Oxford, 1996; Vol. 4; Murakami, Y., Ed., p. 257.
13. Leading refs.: Davis, A. P. Chem. Soc. Rev. 1993, 22, 243. Davis, A. P.; Bonar-Law, R. P.; Sanders, J. K. M. Comprehensive Supramolecular Chemistry; Pergamon: Oxford, 1996; Vol. 4; Murakami, Y., Ed., p. 257.
14. Davis, A. P.; Walsh, J. J. Chem. Commun. 1996, 449. Davis, A. P.; Menzer, S.; Walsh, J. J.; Williams, D. J. Chem. Commun. 1996, 453.
15. Davis, A. P.; Walsh, J. J. Chem. Commun. 1996, 449. Davis, A. P.; Menzer, S.; Walsh, J. J.; Williams, D. J. Chem. Commun. 1996, 453.
16. Davis, A. P.; Perry, J. J.; Williams, R. P. J. Am. Chem. Soc. 1997, 119, 1793.
17. -, had been applied just to 3β-cholestanol (4a). See: Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100. This procedure was not investigated in the present work due to the modest yield reported (60%), and the success of the mesylation described herein.
18. 3) 12.42. 17.28, 22.50, 23.17, 26.50, 26.81, 27.48, 28.16, 30.81, 31.03, 34.60, 34.76, 35.29, 35.35, 35.46, 39.36, 41.84, 41.85, 46.53, 47.20, 51.45, 61.31, 68.24, 73.02, 174.78.
19. Similar regioselectivity has been reported for the conventional Mitsunobu reaction involving 8a and formic acid: Bose, A. K.; Lal, B.; Hoffman, W. A.; Manhas, M. S. Tetrahedron Lett. 1973, 1619.
20. For other examples of convergence through stereodifferentiating inversion, see: Harada, T.; Shintani, T.; Oku, A. J. Am. Chem. Soc. 1995, 117, 12346, refs. cited therein, and discussion in Davis, A. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 591.
21. For other examples of convergence through stereodifferentiating inversion, see: Harada, T.; Shintani, T.; Oku, A. J. Am. Chem. Soc. 1995, 117, 12346, refs. cited therein, and discussion in Davis, A. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 591.
22. The method of Galynker and Still (ref. 5a) is reported to give tosylation with retention of configuration when applied to cholesterol.