An efficient catalytic asymmetric synthesis of chiral γ-butenolides was developed based on the hetero-allylic asymmetric alkylation (h-AAA) in combination with ring closing metathesis (RCM). The synthetic potential of the h-AAA-RCM protocol was illustrated with the facile synthesis of (-)-whiskey lactone, (-)-cognac lactone, (-)-nephrosteranic acid, and (-)-roccellaric acid.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol102994qDOI Listing

Publication Analysis

Top Keywords

ring closing
8
closing metathesis
8
catalytic enantioselective
4
enantioselective synthesis
4
synthesis naturally
4
naturally occurring
4
occurring butenolides
4
butenolides hetero-allylic
4
hetero-allylic alkylation
4
alkylation ring
4

Similar Publications

An Automated Workflow to Discover the Structure-Stability Relations for Radiation Hard Molecular Semiconductors.

J Am Chem Soc

January 2025

Institute of Materials for Electronics and Energy Technology (i-MEET), Department of Materials Science and Engineering, Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Martensstraße 7, 91058 Erlangen, Germany.

Emerging photovoltaics for outer space applications are one of the many examples where radiation hard molecular semiconductors are essential. However, due to a lack of general design principles, their resilience against extra-terrestrial high-energy radiation can currently not be predicted. In this work, the discovery of radiation hard materials is accelerated by combining the strengths of high-throughput, lab automation and machine learning.

View Article and Find Full Text PDF

Developing efficient path integral (PI) methods for atomistic simulations of vibrational spectra in heterogeneous condensed phases and interfaces has long been a challenging task. Here, we present the h-CMD method, short for hybrid centroid molecular dynamics, which combines the recently introduced fast quasi-CMD (f-QCMD) method with fast CMD (f-CMD). In this scheme, molecules that are believed to suffer more seriously from the curvature problem of CMD, e.

View Article and Find Full Text PDF

Background: Atrial flutter (AFL) is usually effectively treated by cavotricuspid isthmus (CTI) ablation. If AFL recurs despite ablation, there is risk of progression to atrial fibrillation (AF) and clinicians should consider underlying structural heart diseases. This consideration becomes especially critical when right-heart-chambers are dilated.

View Article and Find Full Text PDF

The eukaryotic helicase MCM2-7, is loaded by ORC, Cdc6 and Cdt1 as a double-hexamer onto replication origins. The insertion of DNA into the helicase leads to partial MCM2-7 ring closure, while ATP hydrolysis is essential for consecutive steps in pre-replicative complex (pre-RC) assembly. Currently it is unknown how MCM2-7 ring closure and ATP-hydrolysis are controlled.

View Article and Find Full Text PDF

Selective Protein (Post-)modifications through Dynamic Covalent Chemistry: Self-activated SAr Reactions.

J Am Chem Soc

January 2025

Laboratoire de Chimie Supramoléculaire, Institut de Science et d'Ingénierie Supramoléculaires (ISIS), Université de Strasbourg, Strasbourg 67000, France.

SAr reactions were remarkably accelerated using a pretargeting and activating unit based on dynamic covalent chemistry (DCvC). A Cys attack at the C-F bond on the aromatic ring of salicylaldehyde derivatives was only observed upon iminium formation with a neighboring Lys residue of model small peptides. Such self-activation was ascribed to the stronger electron-withdrawing capability of the iminium bond with respect to that of the parent aldehyde that stabilized the transition state of the reaction, together with the higher preorganization of the reactive groups in the cationic aldiminium species.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!