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Molecules 2009, 14(2), 894-903; doi:10.3390/molecules14020894
Article

Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S2-symmetric CD-ring Core

1, 2, 2 and 1,*
Received: 29 January 2009; in revised form: 17 February 2009 / Accepted: 23 February 2009 / Published: 24 February 2009
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Abstract: Three analogues of 1a,25-dihydroxyvitamin D3 (calcitriol), featuring a trans-fused decalin C,D-core with local S2-symmetry, and possessing identical side-chain and seco-B,A-ring structures, have been synthesized starting from readily available (4aR,8aS)-octahydronaphthalene-1,5-dione (7). The very short sequences involve the simultaneous introduction of the side-chain and seco-B,A-ring fragments via Suzuki and Sonogashira coupling reactions. The analogues are devoid of relevant biological activity.
Keywords: Suzuki coupling; Sonogashira reaction; Calcitriol analogues Suzuki coupling; Sonogashira reaction; Calcitriol analogues
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Minne, G.; Verlinden, L.; Verstuyf, A.; De Clercq, P.J. Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S2-symmetric CD-ring Core. Molecules 2009, 14, 894-903.

AMA Style

Minne G, Verlinden L, Verstuyf A, De Clercq PJ. Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S2-symmetric CD-ring Core. Molecules. 2009; 14(2):894-903.

Chicago/Turabian Style

Minne, Garrett; Verlinden, Lieve; Verstuyf, Annemieke; De Clercq, Pierre J. 2009. "Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S2-symmetric CD-ring Core." Molecules 14, no. 2: 894-903.


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