Synthesis of macrocyclic precursors of the vioprolides

Organic & Biomolecular Chemistry
Eibhlin ButlerEric J Thomas

Abstract

The vioprolides are novel depsipeptides that have not been synthesized. However, they have been identified as important targets for synthesis because of their novel biological activities and challenging chemical structures. Following early work on the synthesis of a modified tetrapeptide that contained both the (E)-dehydrobutyrine and thiazoline components of vioprolide D, problems were encountered in taking an (E)-dehydrobutyrine containing intermediate further into the synthesis. A second approach to vioprolides and analogues was therefore investigated in which (E)- and (Z)-dehydrobutyrines were to be introduced by selenoxide elimination very late in the synthesis. A convergent approach to advanced macrocyclic precursors of the vioprolides was then completed using a modified hexapeptide and a dipeptidyl glycerate. In this work, it was necessary to protect the 2-hydroxyl group of the glycerate as its acetate and not as its 2,2,2-trichloroethoxycarbonate. Preliminary studies were carried out on the introduction of the required dehydrobutyrine and thiazoline components into advanced intermediates.

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Citations

Mar 4, 2020·Angewandte Chemie·Hanusch A GrabThorsten Bach
Apr 23, 2020·Natural Product Reports·Per HjerrildThomas B Poulsen
Nov 16, 2019·The Journal of Organic Chemistry·Daniel JoaquinSteven L Castle

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Methods Mentioned

BETA
NMR
column chromatography

Software Mentioned

DAST

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