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

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.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0009-04C5-4 Version Permalink: https://hdl.handle.net/21.11116/0000-0009-04C6-3
Genre: Journal Article

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anie202105732-s1-yiannakas_supporting_information_for_accepted_article.pdf (Supplementary material), 7MB
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 Creators:
Yiannakas, Ektoras1, Author
Grimes, Mark I.1, Author
Whitelegge, James T.1, Author
Fürstner, Alois2, Author           
Hulme, Alison N.1, Author
Affiliations:
1School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ UK, ou_persistent22              
2Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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Free keywords: alkynes; hydrostannation; metathesis; natural products; total synthesis
 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].

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Language(s): eng - English
 Dates: 2021-05-312021-04-272021-06-012021-06-022021-08-16
 Publication Status: Issued
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202105732
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 60 (34) Sequence Number: - Start / End Page: 18504 - 18508 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851