Home
Resources
Publications
Total Synthesis of the Cyclic Depsipeptide Vioprolide D via Its (Z)-Diastereoisomer

Total Synthesis of the Cyclic Depsipeptide Vioprolide D via Its (Z)-Diastereoisomer

Hanusch A Grab, Volker C Kirsch, Stephan A Sieber, Thorsten Bach

Angew Chem Int Ed Engl. 2020 Mar 3.

PMID: 32126146

Abstract:

The first total synthesis of vioprolide D was accomplished in an overall yield of 2.0 % starting from methyl (2S)-3-benzyloxy-2-hydroxypropanoate (16 steps in the longest linear sequence). The cyclic depsipeptide was assembled from two building blocks of similar size and complexity in a modular, highly convergent approach. Peptide bond formation at the C-terminal dehydrobutyrine amino acid of the northern fragment was possible via its (Z)-diastereoisomer. After macrolactamization and formation of the thiazoline ring, the (Z)-double bond of the dehydrobutyrine unit was isomerized to the (E)-double bond of the natural product. The cytotoxicity of vioprolide D is significantly higher than that of its (Z)-diastereoisomer.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP870718073	3-Benzyloxy-2,6-difluorophenylboronic acid		870718-07-3	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: