Journal
CHEMICAL COMMUNICATIONS
Volume 53, Issue 58, Pages 8144-8147Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7cc04690a
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Funding
- Spanish Ministry of Science and Innovation (MSI)
- European Regional Development Fund [SAF2010-15291]
- Xunta de Galicia [GPC2014/001]
- ENDOTHERM GmbH
- Spanish MEI
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Herein, we describe a versatile and efficient total synthesis of 1 alpha, 25-dihydroxyvitamin D-3 (calcitriol). The synthetic strategy relies on an unprecedented Si-assisted S(N)2'-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 alpha, beta, gamma, delta-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.
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