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

Autor: Grab HA; Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747, Garching, Germany., Kirsch VC; Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747, Garching, Germany., Sieber SA; Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747, Garching, Germany., Bach T; Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747, Garching, Germany.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2020 Jul 20; Vol. 59 (30), pp. 12357-12361. Date of Electronic Publication: 2020 Apr 20.
DOI: 10.1002/anie.202002328
Abstrakt: 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.
(© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.)
Databáze: MEDLINE
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