Organic Letters
Organic Letters
5 years ago

Palladium-Mediated Approach to Coumarin-Functionalized Amino Acids

Palladium-Mediated Approach to Coumarin-Functionalized Amino Acids
Christian Hedberg, Tomas Kindahl, Lindon W. K. Moodie, Samy Chammaa
Incorporation of the fluorogenic l-(7-hydroxycoumarin-4-yl)ethylglycine into proteins is a valuable biological tool. Coumarins are typically accessed via the Pechmann reaction, which requires acidic conditions and lacks substrate flexibility. A Pd-mediated coupling is described between o-methoxyboronic acids and a glutamic acid derived (Z)-vinyl triflate, forming latent coumarins. Global deprotection with BBr3 forms the coumarin scaffold in a single step. This mild and scalable route yielded five analogues, including a probe suitable for use at lower pH.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00854

DOI: 10.1021/acs.orglett.7b00854

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