Figure - PMC

Skip to main content

An official website of the United States government

Here's how you know

Here's how you know

Official websites use .gov
A .gov website belongs to an official government organization in the United States.

Secure .gov websites use HTTPS
A lock ( ) or https:// means you've safely connected to the .gov website. Share sensitive information only on official, secure websites.

View full-text article in PMC

. 2019 Mar 22;15:761–768. doi: 10.3762/bjoc.15.72

Search in PMC
Search in PubMed
View in NLM Catalog
Add to search

Copyright © 2019, Ng-Choi et al.

This is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.

The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)

PMC Copyright notice

Scheme 4 — Synthesis of the biaryl bicyclic peptide 3 incorporating a Tyr-Tyr linkage. Reagents and conditions: (i) Piperidine/DMF (3:7). (ii) Fmoc-βAla-OH, DIPCDI, Oxyma, DMF. (iii) Fmoc-Tyr(3-I,Me)-OH, COMU, Oxyma, DIPEA, DMF, overnight. (iv) Fmoc-Gln(Tmob)-OH, DIPCDI, Oxyma, DMF. (v) Fmoc-Leu-OH, DIPCDI, Oxyma, DMF. (vi) Fmoc-Ala-OH, DIPCDI, Oxyma, DMF. (vii) Boc-Tyr(3-B(OH)₂,Me)-OH, DIPCDI, Oxyma, DMF, 3 h. (viii) Pd₂(dba)₃, SPhos, KF, DME/EtOH/H₂O (9:9:2), MW, 120 °C, 30 min. (ix) TFA/H₂O/TIS (95:2.5:2.5), 2 h. (x) TMSOTf, 2,6-lutidine, CH₂Cl₂. (xi) PyOxim, Oxyma, DIPEA, NMP, 24 h.