Synthesis of (S,S)-isodityrosine by Dötz benzannulation.
[reaction: see text] 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.
Gupta
Anuradha
A
Department of Chemistry, University of Missouri-Columbia, Columbia, Missouri 65211, USA.
Sen
Subhabrata
S
Harmata
Michael
M
Pulley
Shon R
SR
D013237:Stereoisomerism; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D014443:Tyrosine; C035129:isodityrosine