Integrin inhibitors based on the tripeptide sequence Arg-Gly-Asp (RGD) are potential therapeutics for the treatment of idiopathic pulmonary fibrosis (IPF). Herein, we describe an expeditious three-step synthetic sequence of Horner–Wadsworth–Emmons olefination, diimide reduction and global deprotection to synthesise cores for these compounds in high yields (63–83% over 3 steps) with no need for chromatography. Key to this transformation is the phosphoramidate protecting group, which is stable to metalation steps.
Keywords: Arginine; Horner–Wadsworth–Emmons; Integrin; Phosphoramidate; Tetrahydronaphthyridine
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Lippa, R. A.; Murphy, J. A.; Barrett, T. Beilstein Arch. 2020, 202055. doi:10.3762/bxiv.2020.55.v1
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