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Angew Chem Int Ed Engl
; 60(34): 18504-18508, 2021 08 16.
Article
in English
| MEDLINE
| ID: mdl-34076945
ABSTRACT
We report the first total synthesis of samroiyotmycinâ 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 ß-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 ].