AI Article Synopsis
Article Abstract
The tetracarbocyclic framework of the nicandrenone natural products is formed in one step from a linear precursor via a domino intramolecular Diels-Alder/intramolecular furan Diels-Alder/aromatization sequence. The approach represents a new 0 → ABCD strategy for the preparation of aromatic steroids.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.5b02412 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Eco-friendly α,β-C(sp)-H difunctionalization of tertiary amines sequential [1,5]-hydride transfer and hetero-Diels-Alder cyclization.
Chem Commun (Camb)
September 2024
Institute of Advanced Studies and School of Pharmaceutical Sciences, Taizhou University, 1139 Shifu Avenue Taizhou, 318000, People's Republic of China.
An unprecedented eco-friendly multi-component domino reaction for the synthesis of novel ,-acetals is reported. The protocol involves sequential coupling, [1,5]-hydride transfer and hetero-Diels-Alder cyclization. This new strategy enables direct α,β-difunctionalization of cyclic amines utilizing enamines generated .
View Article and Find Full Text PDFRapid Access to Divergent Fused Polycycles Via One-Pot A Coupling and Intramolecular Diels-Alder Reaction.
Chemistry
July 2024
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong, China.
Divergent nitrogen-containing fused polycyclic ring systems are constructed from simple starting materials via a one-pot aldehyde-alkyne-amine (A) coupling and intramolecular Diels-Alder reaction. This domino reaction directly furnishes linear 5/5/5 and 5/5/6, or nonlinear 5/5/6/5, polycyclic rings containing an oxa-bridged fused 5/5 bicycle and a 1,6-enyne substructure. One-step derivation of the oxa-bridged 5/5 bicycle leads to a polyfunctionalized 5/5 bicycle with tetrahydrofuran fused back-to-back to pyrroline or a 6/5 bicycle with the hexahydro-1H-isoindole structure, while cycloisomerizing the enyne substructure adds an extra fused 5-membered ring to afford functionalized linear 5/5/5/5 or 5/5/5/5/5 fused ring systems from selected substrates.
View Article and Find Full Text PDFCompeting Domino Knoevenagel-Cyclization Sequences with -Arylcinnamylamines.
J Org Chem
May 2024
Department of Organic Chemistry, University of Debrecen, Debrecen 4002, Hungary.
Domino Knoevenagel-cyclization reactions of -arylcinnamylamines were carried out with active methylene reagents, which took place with five competing cyclization mechanisms: intramolecular hetero Diels-Alder reaction, stepwise polar [2 + 2] cycloaddition, styryl or aza-Diels-Alder reactions followed by rearomatization, and [1,5]-hydride shift-6-endo cyclization. In the stepwise aza-Diels-Alder reaction, the -vinylpyridinium moiety acted as an azadiene, producing a condensed heterocycle with tetrahydroquinolizinium and tetrahydroquiniline subunits. Antiproliferative activity with low micromolar IC values was identified for some of the novel scaffolds.
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 PDFPericyclic Cascade Reactions Affording Thienyl- and Benzo[]thienyl-Fused Architectures: A Synthetic and Density Functional Theory Analysis of Asynchronous Diels-Alder Reactions of Thioarylmaleimides.
J Org Chem
February 2024
Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick E3B 5A3, Canada.
Herein, we report the synthesis and characterization of a series of thioarylmaleimides and their varied propensity toward highly selective domino Diels-Alder (D-A)/rearrangement, D-A/ene/elimination, and D-A/oxidation reactions to give three types of thienyl-fused architectures. Stereochemical assignment was achieved using a combination of nuclear magnetic resonance (NMR) studies, gauge independent atomic orbital (GIAO) NMR chemical shift calculations, and DP4+ analysis. Transition-state calculations support an asynchronous concerted mechanism and provide support for rationalizing the observed regio- and stereoselectivity.
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!