Synthesis of New 26,27-Difluoro- and 26,26,27,27-Tetrafluoro-25-hydroxyvitamin D<sub>3</sub>: Effects of Terminal Fluorine Atoms on Biological Activity and Half-life
Fumihiro Kawagoe, Sayuri Mototani, Kaori Yasuda, Hiroki Mano, Akiko Takeuchi, Hiroshi Saitoh, Toshiyuki Sakaki, Atsushi Kittaka
Abstract
As an extension of our research on providing a chemical library of side-chain fluorinated vitamin D3 analogues, we newly designed and synthesized 26,27-difluoro-25-hydroxyvitamin D3 (1) and 26,26,27,27-tetrafluoro-25-hydroxyvitamin D3 (2) using a convergent method applying the Wittig−Horner coupling reaction between CD-ring ketones (13,14) and A-ring phosphine oxide (5).
Topics & Concepts
ChemistryPhosphine oxideWittig reactionFluorineRing (chemistry)Terminal (telecommunication)Chemical synthesisStereochemistrySide chainBiological activityVitaminPhosphineMedicinal chemistryOrganic chemistryBiochemistryCatalysisComputer scienceTelecommunicationsIn vitroPolymerFluorine in Organic ChemistrySynthesis and Reactions of Organic CompoundsCyclopropane Reaction Mechanisms