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

Ektoras Yiannakas, Mark Grimes, James Whitelegge, Alois Fürstner, Alison Nicola Hulme

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

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].
Original languageEnglish
JournalAngewandte Chemie International Edition
Early online date2 Jun 2021
DOIs
Publication statusE-pub ahead of print - 2 Jun 2021

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