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

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

1, 2, 2 and 1,*
1 artment of Organic Chemistry, Ghent University, Krijgslaan 281, B-9000 Gent, Belgium 2 Laboratory of Experimental Medicine and Endocrinology, Catholic University of Leuven, Gasthuisberg, Herestraat 49, B-3000 Leuven, Belgium
* Author to whom correspondence should be addressed.
Received: 29 January 2009 / Revised: 17 February 2009 / Accepted: 23 February 2009 / Published: 24 February 2009
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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 (CC BY 3.0).

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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.

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