An Alkyne Metathesis Based Approach to the Synthesis of the Anti-malarial 
Macrodiolide Samroiyotmycin A

Yiannakas, Ektoras; Grimes, Mark I.; Whitelegge, James T.; Fürstner, Alois; Hulme, Alison N.

doi:10.1002/anie.202105732

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An Alkyne Metathesis Based Approach to the Synthesis of the Anti-malarial Macrodiolide Samroiyotmycin A

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Yiannakas, E., Grimes, M. I., Whitelegge, J. T., Fürstner, A., & Hulme, A. N. (2021). An Alkyne Metathesis Based Approach to the Synthesis of the Anti-malarial Macrodiolide Samroiyotmycin A. Angewandte Chemie International Edition, 60(34), 18504-18508. doi:10.1002/anie.202105732.

Cite as: https://hdl.handle.net/21.11116/0000-0009-04C5-4

Abstract

We report the first total synthesis of samroiyotmycin A (1), a C₂-symmetric 20-membered anti-malarial macrodiolide isolated from Streptomyces sp. The convergent synthetic strategy orchestrates bisalkyne fragment-assembly using an unprecedented Schӧllkopf-type condensation on a substituted β-lactone and an ambitious late-stage one-pot alkyne cross metathesis–ring-closing metathesis (ACM-RCAM) reaction. The demanding alkyne metathesis sequence is achieved using the latest generation of molybdenum alkylidynes endowed with a tripodal silanolate ligand framework. Subsequent conversion to the required E-alkenes uses contemporary hydrometallation chemistry catalysed by tetrameric cluster [{Cp*RuCl}₄].