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Synthesis of the C-Terminal Macrocycle of Asperipin-2a
Sadegh Shabani1, Jonathan M White1, Craig A Hutton1
1School of Chemistry and Bio21 Molecular Science and Biotechnology Institute , The University of Melbourne , Melbourne , Victoria 3010 , Australia.
Abstract:
A synthetic approach to the C-terminal macrocycle of asperipin-2a is presented. Two epimers were prepared, possessing R- and S-configurations at the β-position of Tyr3. Comparison of NMR data of the natural product with these isomers and X-ray crystallographic data for one macrocycle support assignment of the 2 S,3 S -configuration of Tyr3. Key steps in the synthesis include a stereoselective benzylic oxidation of the tyrosine residue and Lewis-acid-catalyzed ring opening of the subsequently generated aziridine.
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