An efficient synthesis of 1α,25-dihydroxy-20-epi-vitamin D 3

Journal of Steroid Biochemistry and Molecular Biology

Volumn 136, Issue 1, 2013, Pages 14-16

  Fraga, R ^a   Lopez Perez, B ^a   Sokolowska, K ^a   Guini, A ^a   Regueira, T ^a   Diaz, S ^a   Mourino A ^a   Maestro, M A ^b  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

MC1288; Palladium(0) catalyzed coupling; Vitamin D analogues synthesis

Indexed keywords

20 EPICALCITRIOL; ESTER; TRIFLUOROMETHANESULFONIC ACID;

CHEMICAL STRUCTURE; DESILYLATION; METHYLATION; OXIDATION; REVIEW; SYNTHESIS; VITAMIN SYNTHESIS;

EID: 84881169367     PISSN: 09600760     EISSN: 18791220     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2013.01.010     Document Type: Review

References (19)

1. R. Bouillon, A.W. Norman, J.R. Pasqualini(Eds.), Proceedings of the 14th Workshop on Vitamin D, Journal of Steroid Biochemistry and Molecular Biology 121 (2010) 1-478, and the previous 13 volumes in this series.
2. D. Feldman, J.W. Pike, J.S. Adams (Eds.), Vitamin D, 3rd ed., Academic Press, New York, 2011.
3. R. Vieth, The mechanism of vitamin D toxicity, Bone 11 (1990) 267-272.
4. A.J. Brown, A. Dusso, E. Slatopolsky, Selective vitamin D analogs andtheirther-apeutic applications, Seminars in Nephrology 14 (1994) 156-174. (Pubitemid 24083806)
5. L. Binderup, S. Latini, E. Binderup, C. Bretting, M. Calverley, K. Hansen, 20-epi-Vitamin D3 analogues: a potent class of potent regulators of cell growth and immune response, Biochemical Pharmacology 42 (1991) 1569-1575.
6. F.J. Dilworth, M. Calverley, H.L. Makin, G. Jones, Increased biological activity of 20-epi-1a, 25-dihydroxyvitamin D3 is due to reduced catabolism and altered protein binding, Biochemical Pharmacology 47 (1994) 987-993. (Pubitemid 24103830)
7. K. Gumireddy, N. Ikegaki, P.C. Phillips, L.N. Sutton, CD. Reddy, Effect of 20-epi-1a, 25-dihydroxyvitamin D3 on proliferation of human neuroblastoma: role of the cell cycle regulators and the Myc-ID2 pathway, Biochemical Pharmacology 65(2003)1943-1955. (Pubitemid 36629578)
8. (a) M. Calverley, E. Binderup, Preparation of vitamin D analogs, PCT Int. Appl., WO9100271A1 (1991).
9. H. DeLuca, J. Wicha, Method of treating hypoparathyroidism with (20S)-vitamin D3 compounds, US 5552392 A (1996).
10. T. Takahashi, I. Tsuchiguro, Preparation of vitamin D derivatives, Jpn. Kokai Tokkyo Koho, JP 2001329066 A (2001).
11. (d) H. Kashiwagi, Y. Ono, Process for the synthesis of vitamin D compounds and intermediates for the synthesis of the compounds, PCT Int. Appl., WO 2005074389 A2 (2005).
12. (e) A. Bridges, Efficient process for preparing steroids and vitamin D derivatives withthe unnatural configuration at C20 (20 alpha-methyl) from pregnenolone, U.S. Pat. Appl. Publ., US 20080171728 A1 (2008).
13. T. Fujishima, K. Konno, K. Nakagawa, M. Kurobe, T. Okano, H. Takayama, Efficient synthesis and biological evaluation of all A-ring diastereomers of 1a, 25-dihydroxyvitamin D3 and its C-20 epimer, Bioorganic and Medicinal Chemistry 8 (2000) 123-134. (Pubitemid 30125661)
14. P. Gongoi, R. Sigüeiro, S. Eduardo, A. Mouriño, An expeditious route to 1a, 25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed A-ring closure and Suzuki coupling to the C/D unit, Chemistry: A European Journal 16 (2010) 1432-1435.
15. (a) F.J. Sardina, A. Mouriño, L. Castedo, Studies on the synthesis of side-chain metabolites of vitamin D. 2. Stereospecific synthesis of 25-hydroxyvitamin D2, Journal of Organic Chemistry 51 (1986) 1264-1268
16. Y. Fall, C. Barreiro, C. Fernández, A. Mouriño, Vitamin D heterocyclic analogues. Part 1: AstereoselectiveroutetoCD systems with pyrazole rings in their side chains, Tetrahedron Letters 43 (2002) 1433-1436 (Pubitemid 34142429)
17. S. Hatakeyama, M. Yoshino, K. Eto, K. Takahashi, J. Ishihara, Y. Ono, H. Saito, N. Kubodera, Synthesis and preliminary biological evaluation of 20-epi-eldecalcitol [20-epi-1a, 25-dihydroxy-2|3-(3-hydroxypropoxy)vitamin D3: 20-epi-ED-71], Journal of Steroid Biochemistry and Molecular Biology 121 (2010) 25-28.
18. P.J. Garegg, B. Samuelson, Novel reagent system forconverting a hydroxy-group into a iodo-group in carbohydrates with inversión de configuration, Journal of the Chemical Society, Chemical Communications (1979) 978-980.
19. S. Sinishtaj, H.B. Jeon, P. Dolan, T.W. Kensker, G.H. Posner, Highly antiproliferative, low-calcemic, side-chain amide and hydroxymate analogs ofthe hormone 1a, 25-dihydroxyvitamin D3, Bioorganic and Medicinal Chemistry 14 (2006) 6341-6348. (Pubitemid 44224078)