Synthesis of novel analogues of 1alpha,25-dihydroxyvitamin D(3) with side chains at C-18

The Journal of Organic Chemistry
Edelmiro MománAntonio Mouriño

Abstract

Novel analogues of the hormone 1alpha,25-(OH)(2)-D(3) with side chains attached to C-18 were synthesized by a versatile route in which key steps were the remote radical-induced functionalization of the 18-methyl by the C-8beta-hydroxyl group and the introduction of the side chains by Wittig reactions on a C-18-aldehyde. The triene system of the novel analogues was constructed by the convergent Lythgoe-Hoffmann la Roche approach, which involves reaction of a phosphine oxide (the ring A fragment) with a ketone (the upper fragment).

References

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Citations

Apr 29, 2011·Journal of Medicinal Chemistry·Maria A RegueiraMercedes Torneiro
Jan 26, 2008·Chemical Communications : Chem Comm·Faiz Ahmed KhanLaxminarayana Soma
Oct 4, 2013·Chemical & Pharmaceutical Bulletin·Naoyuki KotokuMotomasa Kobayashi
Feb 3, 2006·Natural Product Reports·James R Hanson
May 19, 2020·Organic & Biomolecular Chemistry·Satrajit Indu, Krishna P Kaliappan
Mar 3, 2006·Journal of Medicinal Chemistry·Xosé C González-AviónDino Moras

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