Synthesis 2024; 56(15): 2361-2370
DOI: 10.1055/s-0043-1763750
paper

Synthesis of a Potential Precursor (Northern Fragment) for the Cyclic Depsipeptides Vioprolides A and C

Noé Osorio Reineke
,
Hanusch A. Grab
,
Thorsten Bach
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

Primary Data



Publikationsverlauf

Eingereicht: 04. März 2024

Angenommen nach Revision: 27. März 2024

Artikel online veröffentlicht:
29. April 2024

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