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DOI: 10.1055/s-0043-1763750
Synthesis of a Potential Precursor (Northern Fragment) for the Cyclic Depsipeptides Vioprolides A and C
Financial support from the Deutsche Forschungsgemeinschaft (Ba-1372/23) is gratefully acknowledged.
Abstract
The synthesis of a potential northern fragment for the cyclic depsipeptides vioprolide A and vioprolide C is accomplished. The prepared compound is a pentapeptide and displays the non-canonical amino acid dehydrobutyrine (Dhb) at its C-terminal end. The central position is taken by another non-canonical amino acid, (2S,4R)-4-methylazetidine carboxylic acid (Maz). A route to enantiopure N-Boc-protected Maz (N-Boc-Maz) is developed from l-pyroglutamic acid, and this building block is taken into thiopeptide formation at its C-terminal end by successively coupling serine and threonine fragments. The C-terminal threonine is dehydrated to Dhb before attaching a d-Leu-Ala dipeptide to the N-terminal site of Maz. Several intermediates are directly telescoped into the next reaction step. Starting from N-Boc-Maz, the assembly of the pentapeptide is complete in eight steps with an overall yield of 16%.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1763750.
- Supporting Information
Primary Data
- Primary Data
Primary data for this article are available online at https://zenodo.org/record/10777091 and can be cited using the following DOI: 10.5281/zenodo.10777091.
Publication History
Received: 04 March 2024
Accepted after revision: 27 March 2024
Article published online:
29 April 2024
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For synthetic studies on the vioprolides by other groups, see: