SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 8: 1582 - 1587

DOI: https://doi.org/10.6023/cjoc201402015

Articles

Synthesis of 13α-Substituted-des-C-ring-19-nor-1α,25- dihydroxyvitamin D3 Analogs

  • Cai Zuyun ,
  • DeLuca Hector F.
Expand
  • Department of Biochemistry, College of Agricultural and Life Sciences, University of Wisconsin-Madison, 433 Babcock Drive, Madison, Wl. 53706-1544 USA

Received date: 2014-02-13

  Revised date: 2014-03-27

  Online published: 2014-05-05

Fold

Abstract

The syntheses of 13α-substituted-des-C-ring-19-nor-1α,25-dihydroxyvitamin D3 analogs (12a, 12b) are described. The sequence involves using vitamin D3 as a starting material, cleavage of the six-member ring by Baeyer Villiger reaction, introducing the C-25-hydroxy group by ruthenium oxide, and coupling the D-ring and A-ring by Horner-Witting reaction.

Key words： 13α-substituted; des-C-ring-19-nor-vitamin D3; analogs; synthesis

Cite this article

Cai Zuyun , DeLuca Hector F. . Synthesis of 13α-Substituted-des-C-ring-19-nor-1α,25- dihydroxyvitamin D3 Analogs[J]. Chinese Journal of Organic Chemistry, 2014 , 34(8) : 1582 -1587 . DOI: 10.6023/cjoc201402015

References

[1] Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr. Rev. 1995, 16, 200.
[2] Nishii, Y.; Okano, T. Steroids 2001, 66, 137.
[3] Yamada, S.; Shimizu, M.; Yamamoto, K. Med. Res. Rev. 2003, 23, 89.
[4] Connor, R. I.; Rigby, W. F. C.; Chen, T. C.; Persons, K.; Uskokovic, M. R.; Horst, R. L.; Holick, M. F. Biochem. Biophys. Res. Commun. 1991, 176, 852.
[5] Cai, Z. Y. Chin. J. Org. Chem. 2013, 33, 2244 (in Chinese).
(蔡祖恽, 有机化学, 2013, 33, 2244.)
[6] Ikekawa, N. Med. Res. Rev. 1987, 7, 333.
[7] (a) Norman, A. W.; Manchand, P. S.; Uskokovic, M. R.; Okamura, W. H.; Takeuchi, J. A.; Bishop, J. E.; Hisatake, J.-I.; Koeffler, H. P.; Peleg, S. J. Med. Chem. 2000, 43, 2719.
(b) Saito, N.; Masuda, M.; Saito, H.; Takenouchi, K.; Ishizuka, S.; Namekawa, J.-I.; Takimoto-Kamimura, M.; Kittaka, A. Synthesis 2005, 2533.
(c) Flores, A.; Sicinski, R. R.; Grzywacz, P.; Thoden, J. B.; Plum, L. A.; Clagett-Dame, M.; DeLuca, H. F. J. Med. Chem. 2012, 55, 4352.
(d) Fraga, R.; Zacconi, F.; Sussman, F.; Ordonez-Moran, P.; Munoz, A.; Huet, T.; Molnar, F.; Moras, D.; Rochel, N.; Maestro, M.; Mourino, A. Chem. Eur. J. 2012, 18, 603.
(e) Lu, Y.; Chen, J.; Janjetovic, Z.; Michaels, P.; Tang, E. K. Y.; Wang, J.; Tuckey, R. C.; Slominski, A. T.; Li, W.; Miller, D. D J. Med. Chem. 2012, 55, 3573.
[8] Posner, G. H.; Nelson T. D.; Guyton, K. Z.; Kensler, T. W. J. Med. Chem. 1992, 35, 3280.
[9] Posner, G. H.; Dai, H.; Afarinkia, K.; Murthy, N. N.; Guyton, K. Z.; Kensler, T. W. J. Org. Chem. 1993, 58, 7209.
[10] Posner, G. H.; Lee, J. K.; White, M. C.; Hutchings, R. H.; Dai, H.; Kachinski, J. L.; Dolan, P.; Kensler, T. W. J. Org. Chem. 1997, 62, 3299.
[11] (a) Ono, K.; Yoshida, A.; Saito, N.; Fujishima, T.; Honzawa, S.; Suhara, Y.; Kishimoto, S.; Sugiura, T.; Waku, K.; Takayama, H.; Kittaka, A. J. Org. Chem. 2003, 68, 7407.
(b) Fujishima, T.; Nozaki, T.; Suenaga, T. Bioorg. Med. Chem. 2013, 21, 5209.
[12] (a) Daiben, W. G.; Greenfield, L. J. J. Org. Chem. 1992, 57, 1597.
(b) Kulesza, U.; Sigueiro, R.; Mourino, A.; Sicinski, R. R. J. Org. Chem. 2013, 78, 1444.
[13] Torneiro, M.; Fall, Y.; Castedo, L.; Mourino, A. Tetrahedron Lett. 1992, 33, 105.
[14] Carballa, D. M.; Seoane, S.; Zacconi, F.; Perez, X.; Rumbo, A.; Alvarez-Diaz, S.; Larriba, M. J.; Perez-Fernandez, R.; Munoz, A.; Maestro, M.; Mourino, A. and Torneiro, M. J. Med. Chem. 2012, 55, 8642.
[15] Valles, M. J.; Castedo, L.; Mourino, A. Tetrahedron Lett. 1992, 33, 1503.
[16] Maynard, D. F.; Norman, A. W.; Okamura, W. H. J. Org. Chem. 1992, 57, 3214.
[17] (a) Nilsson, K.; Valles, M. J.; Castedo, L.; Mourino, A.; Halkes, S. J.; van de Velde, J. P. Bioorg. Med. Chem. Lett. 1993, 3, 1855.
(b) Moman, E.; Nicoletti, D.; and Mourino, A. J. Org. Chem. 2004, 69, 4615.
[18] Sabbe, K.; D'Hallewyn, C.; De Clercq, P.; Vandewalle, M.; Bouillon, R.; Verstuyf, A. Bioorg. Med. Chem. Lett. 1996, 6, 1697.
[19] Kutner, A.; Zhao, H.; Fitak, H.; Wilson, S. R. Bioorg. Chem. 1995, 23, 22.
[20] (a) Gabriels, S.; Van Haver, D.; Vandewalle, M.; De Clercq, P.; Verstuyf, A.; Bouillon, R. Chem. Eur. J. 2001, 7, 520.
(b) De Clercq, P.; De Buysser, F.; Minne, G.; Schepens, W.; Vrielynck, F.; Van Haver, D.; Vandewalle, M.; Verstuyf, A.; Bouillon, R. J. Steroid Biochem. Mol. Biol. 2007, 103, 206.
[21] Hans, H.; Beat, W. EP 1094060, 2001[Chem. Abstr. 2001, 134, 295994m].
[22] Plonska-Ocypa, K.; Grzywacz, P.; Sicinski, R. R.; Plum, L. A.; DeLuca, H. F. J. Steroid Biochem. Mol. Biol. 2007, 103, 298.
[23] Sicinski, R. R.; Rotkiewics, P.; Kolinski, A.; Sicinska, W.; Prahl, J. M.; Smith, C. M.; DeLuca, H. F. J. Med. Chem. 2002, 45, 3366.
[24] Peterson, P. E.; Leffew, R. L. B.; Jensen, B. L. J. Org. Chem. 1986, 51, 1948.
[25] Anastasia, M.; Allevi, P.; Ciuffreda, P.; Fiecchi, A.; Scala. A. J. Org. Chem. 1985, 50, 321.
[26] Kiegiel, J.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1991, 32, 6057.
[27] Sicinski, R. R.; DeLuca, H. F. Bioorg. Med. Chem. Lett. 1995, 5, 159.
[28] Carlsen, Per H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
[29] Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Batcho, A. D.; Sereno, J. F.; Uskokovic, M. R. J. Org. Chem. 1986, 51, 3098
[30] Hatakeyama, S.; Numata, H.; Takano, S. Tetrahedron Lett. 1984, 25, 3617.
[31] Diaz, M.; Ferrero, M.; Fernandez, S.; Gotor, V. J. Org. Chem. 2000, 65, 5647.
Options
Outlines

/

〈 〉