Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S2-symmetric CD-ring Core
Pierre J. De Clercq, Annemieke Verstuyf, Lieve Verlinden and 1 more
Molecules · 2009
doi:10.3390/molecules14020894 (opens in a new tab)
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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.
Abstract licence: CC BY
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