American Chemical Society
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Synthesis of (S,S)-Isodityrosine by Dötz Benzannulation

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journal contribution
posted on 2005-09-02, 00:00 authored by Anuradha Gupta, Subhabrata Sen, Michael Harmata, Shon R. Pulley
A synthesis of (S,S)-isodityrosine 1, a naturally occurring, key structural subunit of numerous biologically active macromolecules, is described. A formal [3 + 2 + 1] cycloaddition (Dötz benzannulation) approach was utilized to simultaneously construct an aromatic ring and the diaryl ether linkage in one step. This key step was extended to the synthesis of (S,S)-isodityrosine in two separate convergent synthetic routes. This method demonstrates a novel and mild method for the synthesis of diaryl ethers.