Total Synthesis of 1α,25-Dihydroxy-18-Norvitamin D3

Synlett

Volumn 1997, Issue 10, 1997, Pages 1167-1170

  Sas, B ^a   De Clercq, P ^a   Vandewalle, M ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000343906     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-979     Document Type: Article

References (30)

1. Bouillon, R.; Van Baelen, H. Saudi Med. 1989, 10, 260.
2. DeLuca, H.F.; Burmester, J.; Darwish, H.; Krisinger, J. Comprehensive Medicinal Chemistry, Pergamon Press, New York 1990, vol. 3, 1129.
3. Bouillon, R.; Okamura, W.H.; Norman, A.W. Endocrine Reviews 1995, 16, 200.
4. (a) Bouillon, R.; De Clercq, P.; Pirson, P.; Vandewalle, M. Novel structural analogues of vitamin D; patent PCT/EP 93.202037.3 priority date 09-07-1993;
5. (b) Sabbe, K.; D'Halleweyn, C.; De Clercq, P.; Vandewalle, M.; Bouillon, R.; Verstuyf, A. Bioorg. Med. Chem. Lett. 1996, 6, 1697;
6. (c) Gui-Dong Zhu; Yongjun Chen; Xiaoming Zhou; Vandewalle, M.; De Clercq, P.; Bouillon, R.; Verstuyf, A. Bioorg. Med. Chem. Lett. 1996, 6, 1703;
7. (d) Yong Wu; Ling Shi; D'Halleweyn, C.; Van Haver, D.; De Clercq, P.; Vandewalle, M.; Bouillon, R.; Verstuyf, A. Bioorg. Med. Chem. Lett. 1997, 7, 923.
8. Sicinski, R.R.; Perlman, K.L.; Prahl, J.; Smith, C.; DeLuca, H.F. J. Med. Chem. 1996, 39, 4497.
9. Audia, J.E.; Boisvert, L.; Danishefsky, S.J.; Patten, A.D.; Villalobos, A. J. Org. Chem. 1989, 54, 3738.
10. Cabal, M-P.; Danishefsky, S.J.; Jeroncic, L.O. J. Org. Chem. 1991, 56, 387.
11. Gillis, H.R.; Ko, A.I.; Roush, W.R. J. Am. Chem. Soc. 1982, 104, 2269.
12. Lythgoe, B.; Moran, T.A.; Nambudiry, M.E.N.; Tideswell, J.; Wright, P.W. J. Chem. Soc., Perkin Trans I 1978, 580; Kocienski, P.J.; Lythgoe, B. J. Chem. Soc., Perkin Trans I 1978, 1290.
13. Lythgoe, B.; Moran, T.A.; Nambudiry, M.E.N.; Tideswell, J.; Wright, P.W. J. Chem. Soc., Perkin Trans I 1978, 580; Kocienski, P.J.; Lythgoe, B. J. Chem. Soc., Perkin Trans I 1978, 1290.
14. Baggiolini, E.G.; Iacobelli, J.A.; Hennessey, B.M.; Batcho, A.D.; Sereno, J.F.; Uskokovic, M.R. J. Org. Chem. 1986, 51, 3098.
15. The expected regioselectivity was proven by the COSY spectra of 6 and 7.
16. 3): H-C-OH (3.24, br dt 4.2, 10.3 Hz). For the minor, axial alcohol: H-C-OH 3.78 (br s).
17. Sandheimer, F.; Rozenkranz, G.; Velasco, M. J. Am. Chem. Soc. 1954, 77, 192.
18. Still, W.C.; Mohamadi, F.; Richards, N.G.J.; Guida, W.C.; Lipton, M.; Liskang, R.; Chang, G.; Hendrickson, T.; De Gunst, F.; Hasel, W.; MacroModel V3.0, Department of Chemistry, Colombia University, New York, NY 10027, USA.
19. Barton, D.H.R.; McCombie, S.W. J. Chem. Soc. Perkin 1 1975, 1574.
20. Kwon, Y.C.; Midland, M.M. J. Am. Chem. Soc. 1983, 105, 3725
21. Castedo, L.; Mascareñas, J.L.; Moriño, A.; Sarandeses, L.A. Tetrahedron Lett. 1988, 29, 1203.
22. (a) Wilson, S.R.; Haque, M.S. J. Org. Chem. 1982, 47, 5411.
23. (b) For a review see: Gui-Dong Zhu; Okamura, W.H. Chem. Rev. 1995, 95, 1877.
24. de Jong, C.; de Lange, B.; Feringa, B.L. J. Org. Chem. 1989, 54, 2471.
25. SAM II lipase (Amano Pharm Co, supplied by Fluka).
26. Griffith, W.P.; Ley, V.S. Aldrichim Acta 1990, 23, 13.
27. Oppolzer, W.; Snowder, R.L. Tetrahedron Lett. 1976, 4187.
28. Gui-Dong Zhu; Van Lancker, B.; Van Haver, D.; De Clercq, P. Bull. Soc. Chim. Belg. 1994, 103, 263.
29. Curtin, M.L.; Okamura, W.H. J. Am. Chem. Soc. 1991, 113, 6958.
30. Okamura, W.H.; Midland, M.M.; Hammond, M.W.; Abd. Rahman, N.; Dormanen, M.C.; Nemere, I.; Norman, A.W. J. Steroid. Biochem. Molec. Biol. 1995, 53, 603.