A direct route for the preparation of Fmoc/OtBu protected iodotyrosine. Issue 27 (4th July 2018)

• Record Type: Journal Article
• Authors: Steer, Andrew M.; Bolt, Hannah L.; Brittain, William D.G.; Cobb, Steven L.
• Is Part Of: Tetrahedron letters. Volume 59:Issue 27(2018)
• Page Start: 2644
• Page End: 2646
• Publication Date: 2018-07-04
• Subjects: Amino acid -- Iodotyrosine -- Protecting group -- Bi-aryl -- Suzuki-Miyaura; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.05.061
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Synthesis of an orthogonally protected iodotyrosine which can be directly used in Fmoc SPPS. Iodination reaction conditions optimised. Synthesised iodotyrosine shown to be amenable to Suzuki-Miyaura cross-coupling. Abstract: Herein the synthesis of an Fmoc/O t Bu 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( t Bu)-OH. The Fmoc/O t Bu orthogonally protected iodotyrosine was also shown to be amenable to Suzuki-Miyaura cross-coupling to deliver a novel bi-aryl tyrosine derivative.