Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2020 Aug;34(15):2208-2218.
doi: 10.1080/14786419.2019.1582045. Epub 2019 Apr 2.

Semi-synthesis of a novel hybrid isoxazolidino withaferin via chemoselective and diastereoselective 1,3-dipolar nitrone cycloaddition reaction

Ramkrishna Mandal  1 , Meenakshi Singh  1 , Amrutha A V Krishnan  1 , Yogita H Dahat  1 , Yogesh P Bharitkar  1 , V Ravichandiran  1 , Abhijit Hazra  1
Affiliations

Semi-synthesis of a novel hybrid isoxazolidino withaferin via chemoselective and diastereoselective 1,3-dipolar nitrone cycloaddition reaction

Ramkrishna Mandal et al. Nat Prod Res. 2020 Aug.

Abstract

A facile, atom-economic synthesis of isoxazilidino withaferin, a novel hybrid of withaferin A, has been accomplished via two-step reaction of nitrone synthesis followed by nitrone 1,3-dipolar cycloaddition. The reaction is highly chemoselective (preferential reaction only on one of the two double bonds present on withaferin A) and diastereoselective affording exclusively the cis-fused products. The structure was determined by detailed analysis of 1D, 2D NMR and mass spectral data.

Keywords: 2D NMR (HSQC; COSY; HMBC; NOESY); Withaferin A; isoxazolidine; nitrone-cycloaddition; semi-synthesis.

PubMed Disclaimer

LinkOut - more resources