56630-32-1Relevant academic research and scientific papers
An Alkyne-Metathesis-Based Approach to the Synthesis of the Anti-Malarial Macrodiolide Samroiyotmycin A
Fürstner, Alois,Grimes, Mark I.,Hulme, Alison N.,Whitelegge, James T.,Yiannakas, Ektoras
, p. 18504 - 18508 (2021/07/26)
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 Sch?llkopf-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].
Synthesis, Characterization, and Stereochemistry of Bridged Intramolecularly Alkylated Cobaloximes; Monomeric and Dimeric Complexes of Different Configuration
Robinson, John A.,Flohr, Helmut,Kempe, Uwe Max,Pannhorst, Wolfgang,Retey, Janos
, p. 181 - 203 (2007/10/02)
Ligands have been synthesized containing two vicinal dioxime functions joined by a carbon chain to which is attached in the centre a bromomethyl or chloromethyl group (20, 22, 25).These ligands, upon reaction with cobalt(II) chloride in the presence of pyridine and sodium borohydride afforded bridged intramolecularly alkylated cobaloximes.When the vicinal dioxime functions are separated by a chain of nine carbon atoms mainly dimeric complexes are formed.Two of these, 26 and 27, were isolated and characterized by spectroscopic methods and their structures were established by X-ray crystallography.Ligands containing eleven or thirteen carbon atoms between the dioxime functions afforded mainly monomeric cobaloximes with cis configuration, e. g. 28.The trans-monomeric complex 30 was produced along with the cis isomer when the number of carbon atoms in the bridge was raised to fifteen.
