Issue 61, 2014

Efficient and scalable total synthesis of calcitroic acid and its 13C-labeled derivative

Abstract

Calcitroic acid, the deactivated form of the physiological active vitamin D3 metabolite calcitrol, and its 13C labeled derivative has been synthesized starting from the commercially available Inhoffen-Lythgoe diol in 11 steps with an overall yield of 21%. The key steps in the synthesis were the formation of the C1-homologated nitrile with KCN and K13CN as well as the Horner–Wittig reaction with the ring A phosphine oxide reagent.

Graphical abstract: Efficient and scalable total synthesis of calcitroic acid and its 13C-labeled derivative

Supplementary files

Article information

Article type
Paper
Submitted
09 May 2014
Accepted
10 Jul 2014
First published
14 Jul 2014

RSC Adv., 2014,4, 32327-32334

Author version available

Efficient and scalable total synthesis of calcitroic acid and its 13C-labeled derivative

D. Meyer, L. Rentsch and R. Marti, RSC Adv., 2014, 4, 32327 DOI: 10.1039/C4RA04322G

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