A synthesis of 17-epi-calcidiol |
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| Authors: | Alicja Kurek-Tyrlik |
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| Institution: | Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44, 01-224 Warsaw, Poland |
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| Abstract: | The first synthetic approach to 17-epi-calcidiol 4 and congeners is presented. Key steps of the synthesis involve Pd-catalyzed reaction of the androst-16-ene derivative 6 with alkyl diazoacetates producing the respective cyclopropane derivatives 5, and lithium in liquid ammonia reduction of 5 leading to 17α-pregnane-20-carboxylic acid derivatives 9. The side chain was attached to ester 19 in a known manner. |
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| Keywords: | Vitamin D synthesis Cyclopropanation Alkyl diazoacetates Lithium in liquid ammonia |
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