Asymmetric synthesis of 1 α,25-dihydroxyvitamin D3 A-ring precursor starting with 5-tert-butyldimethylsiloxy-2-cyclohexenone

Tetrahedron Letters

Volumn 41, Issue 14, 2000, Pages 2385-2388

  Hareau, Georges P J ^a   Koiwa, Masakazu ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric synthesis; Hydroxylation; Selective protection; Vitamins

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; CALCITRIOL DERIVATIVE;

ARTICLE; HYDROXYLATION; PRECURSOR; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034175643     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00169-6     Document Type: Article

References (26)

1. (a) Hikichi, S.; Hareau, G. P. J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299.
2. (b) Hareau, G. P. J.; Hikichi, S.; Sato, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2099.
3. (c) Hareau, G. P. J.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640.
4. (d) Hareau, G. P. J.; Koiwa, M.; Hanazawa, T.; Sato, F. Tetrahedron Lett. 1999, 40, 7493;
5. see also: (e) Koiwa, M.; Morizono, D.; Hareau, G. P. J.; Sato, F. Tetrahedron Lett. 1999, 40, 4199.
6. Zhu G.-D.; Okamura, W. H. Chem Rev. 1995, 95, 1877.
7. (a) Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Uskokovic, M. R. J. Am. Chem. Soc. 1982, 104, 2945.
8. (b) Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Batcho, A. D.; Sereno, J. F.; Uskokovic, M. R. J. Org. Chem. 1986, 51, 3098.
9. (a) Kobayashi, S.; Shibata, J.; Shimada, M.; Ohno, M. Tetrahedron Lett. 1990, 31, 1577.
10. (b) Posner, G. H.; Kinter, C. M. J. Org. Chem. 1990, 55, 3967.
11. (c) Nagasawa, K.; Zako, Y.; Ishihara, H.; Shimizu, I. Tetrahedron Lett. 1991, 32, 4937. Nagasawa, K.; Ishihara, H.; Zako, Y.; Shimizu, I. J. Org. Chem. 1993, 58, 2523.
12. (c) Nagasawa, K.; Zako, Y.; Ishihara, H.; Shimizu, I. Tetrahedron Lett. 1991, 32, 4937. Nagasawa, K.; Ishihara, H.; Zako, Y.; Shimizu, I. J. Org. Chem. 1993, 58, 2523.
13. (d) Chen, C.; Crich, D. Tetrahedron Lett. 1992, 33, 1945. Chen, C.; Crich, D. Tetrahedron 1993, 49, 7943.
14. (d) Chen, C.; Crich, D. Tetrahedron Lett. 1992, 33, 1945. Chen, C.; Crich, D. Tetrahedron 1993, 49, 7943.
15. (e) Stork, G.; Hutchinson, D.; Okabe, M.; Parker, D.; Ra, C.; Ribereau, F.; Suzuki, T.; Zebovitz, T. Pure Appl. Chem. 1992, 64, 1809.
16. (f) Tazumi, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1994, 1903.
17. (g) Hatakeyama, S.; Irie, H.; Shintani, T.; Noguchi, Y.; Yamada, H.; Nishizawa, M. Tetrahedron 1994, 50, 13369.
18. (h) Mourino, A.; Torneiro, M.; Vitale, C.; Fernandez, S.; Perez-Sestlo, J.; Anne, S.; Gregorio, C. Tetrahedron Lett. 1997, 38, 4713.
19. 2tert-Bu into the mixture of 6 and zinc in trimethyl borate-THF; thus, it might cause trouble when carried out on a large scale.
20. 3..
21. (a) Takai, K.; Hotta, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1978, 2417.
22. (b) Lombardo, L. Tetrahedron Lett. 1982, 23, 4293.
23. 2Et) rather than the tert-butyl ester series, but in the methylenation step, the corresponding 10 further reacted with the Lombardo reagent at the ethyl ester functionality, thus producing the methyl ketone 10 (Σ=COMe) in a somehow uncontrollable yield; we then switched to the tert-butyl ester series where the formation of the methyl ketone has not been observed.
24. Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413.
25. Tsuji, J. Palladium Reagents in Organic Synthesis; John Wiley & Sons, 1995.
26. Jones, A. B.;Villalobos, A.; Robert, G. L.; Danishefsky, S. J. J. Org. Chem. 1990, 55, 2786.