Ring-rearrangement metathesis (RRM) refers to the combination of several metathesis transformations into a domino process, in which an endocyclic double bond of a cycloolefin reacts with an exocyclic alkene. RRM has proven to be a powerful method for the rapid construction of complex structures. The extension of the basic ring-opening-ring-closing metathesis process by further metathesis steps as well as an examination of the driving forces, limits, scope, recent advantages, and future perspectives of these domino sequences is presented with various examples, thus reflecting the high efficiency and utility of RRM in organic synthesis.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/asia.200700072 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Formal Synthesis of (+)-Sinefungin by Way of Sequential Asymmetric Metal Catalysis.
Org Lett
May 2024
Department of Chemistry, Pohang University of Science and Technology, 77 Cheongam-Ro, Pohang, Kyungbuk 37673, Republic of Korea.
Here, we report a approach toward (+)-sinefungin, a potent inhibitor of the physiological methyl transfer process. A key feature is represented by the sequential metal catalysis combining Pd-catalyzed hydroalkoxylation and ring-rearrangement metathesis. The unique advantage of the method is highlighted by the unprecedented complete control of the C stereocenter.
View Article and Find Full Text PDFSynthetic Approach toward Diverse Oxa-Cages via Olefin Metathesis.
J Org Chem
May 2024
Department of Chemistry, Indian Institute of Technology, Powai, Mumbai 400076, India.
This article demonstrates a late-stage modification of the cage propellanes that are transformed into intricate oxa-cycles via ring-rearrangement metathesis (RRM) and regioselective ring-closing metathesis (RCM) as crucial steps. In addition, we also report the extended pentacycloundecane (PCUD)-based oxa-cages involving the domino cycloetherification followed by olefin metathesis. These oxa-cages involve a domino sequence in which the PCUD core unit remains intact.
View Article and Find Full Text PDFStereocontrolled synthesis of some novel functionalized heterocyclic amino ester and amide derivatives with multiple stereocenters.
RSC Adv
July 2023
Institute of Organic Chemistry, Stereochemistry Research Group, Research Centre for Natural Sciences Magyar tudósok krt. 2 H-1117 Budapest Hungary +36-30-1600354.
The synthesis of some novel functionalized fused-ring β-amino lactones and lactams with multiple chiral centers has been attempted from readily available strained bicyclic β-amino acids a stereocontrolled synthetic route. The key step was ring-rearrangement metathesis of allyl/propargyl esters or -allylated/-propargylated amides of (oxa)norbornene β-amino acids. The RRM transformations [ring-opening metathesis (ROM)/ring-closing metathesis (RCM) or ring-opening metathesis (ROM)/ring-closing enyne metathesis (RCEYM)] have been investigated using some commercially available catalysts.
View Article and Find Full Text PDFMolecular Acrobatics in Polycyclic Frames: Synthesis of "Kurmanediol" via Post-synthetic Modification of Cage Molecules by Olefinic Metathesis.
J Org Chem
August 2023
Department of Chemistry, Institution Indian Institute of Technology, Powai, Mumbai 400076, India.
We report late-stage ring-opening metathesis (ROM), ring-rearrangement metathesis (RRM), and ring-closing metathesis (RCM) approaches to generate expanded pentacycloundecane (PCUD) cage derivatives. These higher-order intricate polycyclic cage systems are aesthetically pleasing and structurally intriguing. Their assembly maintains molecular symmetry during the entire synthetic sequence.
View Article and Find Full Text PDFA Modular Approach to Angularly Fused Polyquinanes via Ring-Rearrangement Metathesis: Synthetic Access to Cameroonanol Analogues and the Basic Core of Subergorgic Acid and Crinipellin.
J Org Chem
December 2021
Department of Chemistry, Indian Institute of Technology-Bombay, Powai, Mumbai 400 076, India.
We describe a modular approach to angularly fused polyquinanes that are core units of many natural products such as cameroonanol, subergorgic acid, and crinepellin, etc. in excellent yields by employing atom-economic ring-rearrangement metathesis as a key step. Our work highlights, the synthesis of cameroonanol analogues - and their ester derivatives by using the stereoselective reduction of the carbonyl group by using DIBAL-H- and DCC-mediated coupling as the key reactions.
View Article and Find Full Text PDFWant 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!