Abstract
Herein the synthesis of an Fmoc/OtBu orthogonally protected iodotyrosine derivative is reported. This has been achieved via a simple two-step process in an overall 58% yield from commercially available Fmoc-Tyr(tBu)-OH. The Fmoc/OtBu orthogonally protected iodotyrosine was also shown to be amenable to Suzuki-Miyaura cross-coupling to deliver a novel bi-aryl tyrosine derivative.
Highlights
Halogenated aromatic amino acids represent an important class of building blocks which have been utilised for a myriad of applications
Applying their bis(pyridine)iodinium tetrafluoroborate (IPy2BF4) mediated reaction conditions to Fmoc-Tyr(tBu)-OH 5 did lead to iodination, but with concomitant removal of the tBu group to yield compound 6 in
In order to combat this, less acidic reaction conditions were sought. This led us to explore the combination of iodine and silver sulfate in methanol which had been previously reported to deliver a range of iodotyrosines in excellent yields but not the desired target 4.21
Summary
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