Lactones: classification, synthesis, biological activities, and industrial applications

Although alkyne metathesis has been known for 50 years, rapid progress in this field has mostly occurred during the last two decades. In this article, the development of several highly efficient and thoroughly studied alkyne metathesis catalysts is reviewed, which includes novel well-defined, in situ formed and heterogeneous systems. Various alkyne metathesis methodologies, including alkyne cross-metathesis (ACM), ring-closing alkyne metathesis (RCAM), cyclooligomerization, acyclic diyne metathesis polymerization (ADIMET), and ring-opening alkyne metathesis polymerization (ROAMP), are presented, and their application in natural product synthesis, materials science as well as supramolecular and polymer chemistry is discussed. Recent progress in the metathesis of diynes is also summarized, which gave rise to new methods such as ring-closing diyne metathesis (RCDM) and diyne cross-metathesis (DYCM).

Well‐Defined Alkyne Metathesis Catalysts: Developments and Recent Applications

The highly cytotoxic cyclodepsipeptides of the nannocystin family are known to bind to the eukaryotic translation elongation factor 1α (EF-1α). Analysis of the docking pose, as proposed by a previous in silico study, suggested that the trisubstituted alkene moiety and the neighboring methyl ether form a domain that might be closely correlated with biological activity. This hypothesis sponsored a synthetic campaign which was designed to be “motif-oriented”: specifically, a sequence of ring closing alkyne metathesis (RCAM) followed by hydroxy-directed trans-hydrostannation of the resulting cycloalkyne was conceived, which allowed this potentially anchoring substructure to be systematically addressed at a late stage. This inherently flexible approach opened access to nannocystin Ax (1) itself as well as to 10 non-natural analogues. While the biological data confirmed the remarkable potency of this class of compounds and showed that the domain in question is indeed an innate part of the pharmacophore, the spe...

/pdf/a-motif-oriented-total-synthesis-of-nannocystin-ax-4rhjed9yvq.pdf

A "Motif-Oriented" Total Synthesis of Nannocystin Ax. Preparation and Biological Assessment of Analogues.

Tuning the Catalytic Alkyne Metathesis Activity of Molybdenum and Tungsten 2,4,6-Trimethylbenzylidyne Complexes with Fluoroalkoxide Ligands OC(CF3)nMe3–n (n = 0–3)

Studies on Molybdena- and Tungstenacyclobutadiene Complexes Supported by Fluoroalkoxy Ligands as Intermediates of Alkyne Metathesis

Identification of a Grain Beetle Macrolide Pheromone and Its Synthesis by Ring-Closing Metathesis Using a Terminal Alkyne

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Identification of a Grain Beetle Macrolide Pheromone and Its Synthesis by Ring-Closing Metathesis Using a Terminal Alkyne