Stereoselective Synthesis and Biological Evaluation of ent‐Asperolide C and its Analogues

Authors:
Publisher website
Google Scholar
Abstract
A stereoselective synthesis of ent‐asperolide C and its analogues is described. A chiral‐pool approach was used with a linear sequence of 10 steps, starting from readily available and inexpensive andrographolide. The approach features the construction of a five‐membered lactone skeleton with suitable chiral centres from andrographolide through diastereoselective epoxidation of the exocyclic double bond, and tandem oxidative cleavage of the C‐14=C‐15 double bond and subsequent epoxide ring opening. The stereochemistry of 8 was established by X‐ray crystallographic analysis. Four analogues of ent‐asperolide C were synthesized, and their biological activities were evaluated against A539 and HeLa cell lines. Compound 12 was found to show a weak to moderate antiproliferation effect against both cell lines.

This publication has 25 references indexed in Scilit: