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Issue 58, 2017
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Total synthesis of 1α,25-dihydroxyvitamin D3 (calcitriol) through a Si-assisted allylic substitution

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Abstract

Herein, we describe a versatile and efficient total synthesis of 1α,25-dihydroxyvitamin D3 (calcitriol). The synthetic strategy relies on an unprecedented Si-assisted SN2′-syn displacement of carbamates by cuprates to set the challenging pivotal quaternary methyl group at the fused-ring junction of the CD-trans-hydrindane core. Other key transformations involve the catalytic asymmetric reduction of an α,β,γ,δ-unsaturated ester with CuH to generate the natural steroidal configuration at C20 and a Pauson–Khand cyclization to form the CD-ring skeleton. This strategy enables the syntheses of novel analogs for structure-function studies and drug development.

Graphical abstract: Total synthesis of 1α,25-dihydroxyvitamin D3 (calcitriol) through a Si-assisted allylic substitution

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Publication details

The article was received on 16 Jun 2017, accepted on 28 Jun 2017 and first published on 28 Jun 2017


Article type: Communication
DOI: 10.1039/C7CC04690A
Citation: Chem. Commun., 2017,53, 8144-8147
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    Total synthesis of 1α,25-dihydroxyvitamin D3 (calcitriol) through a Si-assisted allylic substitution

    B. López-Pérez, M. A. Maestro and A. Mouriño, Chem. Commun., 2017, 53, 8144
    DOI: 10.1039/C7CC04690A

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