Issue 58, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
16 Jun 2017
Accepted
28 Jun 2017
First published
28 Jun 2017

Chem. Commun., 2017,53, 8144-8147

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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