Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 18, Pages 7422-7425Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo050363n
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- NIGMS NIH HHS [GM59350-01] Funding Source: Medline
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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 (Dotz 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.
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