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Synlett 2021; 32(03): 273-276
DOI: 10.1055/a-1282-6870
DOI: 10.1055/a-1282-6870
letter
Total Synthesis of Allene-Containing Cyclic Tetrapeptide Pseudoxylallemycin C
A.J.C. thanks Lottery Health Research for a Postdoctoral Fellowship (Grant Number 2019-100659).
Abstract
The first total synthesis of the allene-containing cyclic tetrapeptide pseudoxylallemycin C is reported. The Tyr(t-Bu)-protected linear peptide was prepared on-resin and cyclized in solution phase to yield the protected cyclic precursor. Upon deprotection of Tyr(t-Bu), the desired phenolic cyclic tetrapeptide was separated by RP-HPLC from its epimer that also formed during the macrocyclisation step. Subsequent alkylation with 4-bromobuta-1,2-diene yielded pseudoxylallemycin C.
Key words
allene - cyclic tetrapeptide - cyclization - pseudoxylallemycin - natural product - total synthesis - T3PSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1282-6870.
- Supporting Information
Publication History
Received: 10 September 2020
Accepted after revision: 05 October 2020
Accepted Manuscript online:
05 October 2020
Article published online:
02 November 2020
© 2020. Thieme. All rights reserved
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