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Synthesis 2019; 51(08): 1791-1794
DOI: 10.1055/s-0037-1612060
DOI: 10.1055/s-0037-1612060
paper
Efficient Synthesis of a 5α-Reductase Inhibitor, 3-(Tetrazol-5-yl)-3,5-pregnadien-20-one through Allylic Rearrangement of Cyanophosphates
This work was supported financially by research funds from Osaka University of Pharmaceutical Sciences.Further Information
Publication History
Received: 28 November 2018
Accepted after revision: 06 December 2018
Publication Date:
29 January 2019 (online)
Abstract
We describe the use of allylic rearrangements of cyanophosphates for the efficient and practical synthesis of 3-(tetrazol-5-yl)-3,5-pregnadien-20-one, which is a potent 5α-reductase inhibitor (IC50: 15.6 nM), from pregnene-3,20-dione in 92% overall yield in four steps.
Key words
synthesis - DEPC - cyanophosphates - allylic rearrangement - 3-(tetrazol-5-yl)-3,5-pregnadien-20-one - 5AR inhibitorSupporting Information
- Supporting Information for this article is available online at https://doi.org/10.1055/s-0037-1612060. Included are investigations of the reaction mechanism for the transformation of enone CPs into dienes, and 1H and 13C NMR spectra for compounds 2 and 4.
- Supporting Information
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For the recent reviews on DEPC and CPs, see:
For recent reviews on tetrazoles, see: