A novel synthesis of beta-lactam fused cyclic enediynes by intramolecular Kinugasa reaction.

Chem Commun (Camb)

Bioorganic Laboratory, Department of Chemistry, Indian Institute of Technology, Kharagpur, India.

Published: July 2006

A general synthetic route to beta-lactam-fused enediynes by intramolecular Kinugasa reaction has been successfully developed. The method has widened the scope of Kinugasa reaction in the synthesis of sensitive systems like the one described in this communication.

Download full-text PDF

Source
http://dx.doi.org/10.1039/b605743hDOI Listing

Publication Analysis

Top Keywords

kinugasa reaction
12
enediynes intramolecular
8
intramolecular kinugasa
8
novel synthesis
4
synthesis beta-lactam
4
beta-lactam fused
4
fused cyclic
4
cyclic enediynes
4
reaction general
4
general synthetic
4

Similar Publications

The β-lactam scaffolds are the prevalent structural units in antibiotics and natural products. Herein, three-component asymmetric Kinugasa/aldol and Kinugasa/Mannich cascade reactions have been developed for constructing α-quaternary chiral β-lactams. This method involved the tandem reaction of alkynes, nitrones and aldehydes (or imines), resulting in the formation of three sequential stereocenters controlled by copper(I) catalysts and chiral bis(oxazolidine) ligands.

View Article and Find Full Text PDF

A mild copper-catalyzed asymmetric Kinugasa/Michael addition cascade process is developed. The reaction of α, β-unsaturated ester-tethered propiolamides with nitrones provides an efficient protocol for the construction of functionalized chiral 2,6-diazaspiro[3.4]octane-1,5-dione products in satisfactory yields and with high enantio- and diastereoselectivities.

View Article and Find Full Text PDF

Stereoselective Kinugasa/Aldol Cyclization: Synthesis of Enantioenriched Spirocyclic β-Lactams.

Org Lett

December 2023

Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.

We report an enantioselective copper-catalyzed Kinugasa/aldol domino reaction. This strategy enables access to a range of spirocyclic β-lactam pyrrolidinones in a stereoselective fashion. Under mild reaction conditions, prochiral alkyne-tethered ketones are coupled with nitrones to enable the facile construction of two spirofused ring systems containing three continuous stereocenters with excellent enantioselectivity.

View Article and Find Full Text PDF

Introduction: Bacteroides fragilis (B. fragilis) is considered to act in an anti-inflammatory manner on the intestinal tract. On the contrary, enterotoxigenic B.

View Article and Find Full Text PDF

Although mRNA coronavirus disease 2019 (COVID-19) vaccines have been reported for high effectiveness against symptoms, it remains unclear whether post-vaccination infections are less symptomatic than infections in vaccine-naive individuals. We included patients with COVID-19 diagnosed by polymerase chain reaction tests during Japan's alpha and delta variant epidemics. COVID-19 symptoms at approximately 4 weeks were compared based on COVID-19 vaccination status.

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!