Bioinspired synthesis and biological evaluation of -protulactones A and B.

Org Biomol Chem

State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.

Published: December 2023

AI Article Synopsis

  • The research focused on creating two specific lactones, (-)-protulactone A and (+)-protulactone B, using innovative methods inspired by nature and a chiron approach.
  • The synthesis process involved efficient one-pot reactions that combined multiple steps to simplify the procedure and reduce purification efforts.
  • The synthesized compounds were tested for their ability to inhibit cancer cell growth in certain tumor lines (like MCF-7 and Capan 2) but demonstrated only minor cytotoxic effects.

Article Abstract

The bioinspired and stereoselective synthesis of the furo[3,2-] furan lactone (-)-protulactone A and the dioxabicyclo[3.3.1]nonane lactone (+)-protulactone B has been achieved based on the chiron approach. The synthesis features the utilization of a number of one-pot, sequential transformations, including a cascade reaction of reductive elimination and nucleophilic addition in a one-pot process and a one-pot sequence cross-metathesis/acetonide deprotection/O-Michael addition/lactonization to streamline the synthesis route and avoid the tedious work of product purification. Synthetic protulactones and their analogues were evaluated for their antiproliferative activity against selected tumor cell lines (MCF-7 and Capan 2) and showed minor cytotoxicity.

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Source
http://dx.doi.org/10.1039/d3ob01708gDOI Listing

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