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Synlett 2021; 32(03): 273-276
DOI: 10.1055/a-1282-6870
letter

Total Synthesis of Allene-Containing Cyclic Tetrapeptide Pseudoxylallemycin C

Alan J. Cameron∗
a   School of Chemical Sciences, The University of Auckland, 23 Symonds St., Auckland 1010, New Zealand
b   School of Biological Sciences, The University of Auckland, 3A Symonds St., Auckland 1010, New Zealand
c   Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3A Symonds St., Auckland 1010, New Zealand   Email: alan.Cameron@auckland.ac.nz   Email: m.Brimble@auckland.ac.nz
,
Casey Park
a   School of Chemical Sciences, The University of Auckland, 23 Symonds St., Auckland 1010, New Zealand
b   School of Biological Sciences, The University of Auckland, 3A Symonds St., Auckland 1010, New Zealand
,
Georgina K. Howard
a   School of Chemical Sciences, The University of Auckland, 23 Symonds St., Auckland 1010, New Zealand
,
Paul W. R. Harris 
a   School of Chemical Sciences, The University of Auckland, 23 Symonds St., Auckland 1010, New Zealand
b   School of Biological Sciences, The University of Auckland, 3A Symonds St., Auckland 1010, New Zealand
c   Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3A Symonds St., Auckland 1010, New Zealand   Email: alan.Cameron@auckland.ac.nz   Email: m.Brimble@auckland.ac.nz
,
Margaret A. Brimble  ∗
a   School of Chemical Sciences, The University of Auckland, 23 Symonds St., Auckland 1010, New Zealand
b   School of Biological Sciences, The University of Auckland, 3A Symonds St., Auckland 1010, New Zealand
c   Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3A Symonds St., Auckland 1010, New Zealand   Email: alan.Cameron@auckland.ac.nz   Email: m.Brimble@auckland.ac.nz
› Author AffiliationsA.J.C. thanks Lottery Health Research for a Postdoctoral Fellowship (Grant Number 2019-100659).
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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 - T3P

Supporting 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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