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Issue 24, 2018
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Total synthesis of 1α,25-dihydroxyvitamin D3 analogs modified at the side chain and D-ring

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Abstract

Herein, we describe a synthetic strategy to access 1α,25-dihydroxyvitamin D3 (calcitriol) analogs with natural or unnatural configuration at C20 and unsaturation at the D-ring. The synthetic approach is exemplified by the synthesis of two potent analogs, namely 1α,25-dihydroxy-16-en-23-yne-vitamin D3 and 1α,25-dihydroxy-20-epi-24a-homo-26,27-dimethyl-vitamin D3. A key feature of the synthetic strategy is the generation of an unnatural configuration at C20 by a catalytic asymmetric reduction of an α,β,γ,δ-unsaturated ester with the CuH species in a micellar system.

Graphical abstract: Total synthesis of 1α,25-dihydroxyvitamin D3 analogs modified at the side chain and D-ring

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Publication details

The article was received on 29 Apr 2018, accepted on 29 May 2018 and first published on 30 May 2018


Article type: Paper
DOI: 10.1039/C8OB01002A
Citation: Org. Biomol. Chem., 2018,16, 4563-4569
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    Total synthesis of 1α,25-dihydroxyvitamin D3 analogs modified at the side chain and D-ring

    B. López-Pérez, M. A. Maestro and A. Mouriño, Org. Biomol. Chem., 2018, 16, 4563
    DOI: 10.1039/C8OB01002A

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