Abstract
AbstractWe 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 Schöllkopf‐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].
Highlights
In 2013, Pittayakhajonwut and co-workers reported that the crude extracts of Streptomyces sp
Examining the ACM–RCAM step, both ACM and RCAM reactions of ynoates have been explored in isolation previously, the number of successful examples is small,[17,18,19,20,21,22,23] likely because electron-deficient triple bonds in general are poorly reactive and ynoates in particular were beyond reach of the classical catalysts.[24,25]
To our knowledge there are no examples of a one-pot ynoate ACM–RCAM, as
Summary
Citation for published version: Yiannakas, E, Grimes, M, Whitelegge, J, Fürstner, A & Hulme, AN 2021, 'An Alkyne Metathesis Based Approach to the Synthesis of the Antimalarial Macrodiolide Samroiyotmycin A', Angewandte Chemie International Edition. Link: Link to publication record in Edinburgh Research Explorer Document Version: Publisher's PDF, known as Version of record
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