A practical synthesis of A-ring precursors for 19-nor-1α,25-dihydroxyvitamin D3 analogues

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7637-7640

  Zhou, Sheng Ze ^a   Anné, Sofia ^a   Vandewalle, Maurits ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CALCITRIOL DERIVATIVE; COLECALCIFEROL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030583476     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01700-5     Document Type: Article

References (16)

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3. 3. (a)Perlman, K.L.; Sicinski, R.R.; Schnoes, H.K.; DeLuca, H.F. Tetrahedron Lett. 1990, 31, 1823;
4. (b) Perlman, K.L.; Swenson, R.E.; Paaren, H.E.; Schnoes, H.K.; DeLuca, H.F. Tetrahedron Lett. 1991, 32, 7663.
5. 4. Bouillon, R.; Sarandeses, A.; Allewaert, K.; Zhao, J.; Mascareñas, J.; Mouriño, A. Vrielynck, S.; De Clercq, P. Vandewalle, M. J. Bone & Min. Res. 1993, 8, 1009.
6. 5. Pei-qiang, H.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299.
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10. 9. Rychnovsky, S.P.; Griesgraber, G.; Zeller, S.; Skalitzky, D.J. J. Org. Chem. 1991, 56, 5161.
11. 10. Lythgoe, B.; Moran, T.A.; Nambudiry, M.E.N.; Tideswell, J.; Wright, P.W. J. Chem. Soc., Perkin Trans. I 1978, 590; Kocienski, P.J.; Lythgoe, B. J. Chem. Soc., Perkin Trans. I 1978, 1290.
12. 10. Lythgoe, B.; Moran, T.A.; Nambudiry, M.E.N.; Tideswell, J.; Wright, P.W. J. Chem. Soc., Perkin Trans. I 1978, 590; Kocienski, P.J.; Lythgoe, B. J. Chem. Soc., Perkin Trans. I 1978, 1290.
13. 11. In this synthesis the TBDPS protective group was choosen instead of TBS (ref. 5) because we have observed that 3a and 4a are rather volatile during oil pump drying.
14. 12. Corey, E.J.; Borden, W.T. Tetrahedron Lett. 1984, 313.
15. 13. Trost, B.M.; Dumas, J.; Villa, M. J. Am. Chem. Soc. 1992, 114, 9836.
16. 1H NMR : compare ref. 5.