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Total Syntheses and Biological Evaluation of 3‐ O ‐Methylfunicone and Its Derivatives Prepared by TMPZnCl·LiCl‐Mediated Halogenation and Carbonylative Stille Cross‐Coupling
Author(s) -
Ehrlich Michael,
Carell Thomas
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201256
Subject(s) - stille reaction , chemistry , halogenation , regioselectivity , natural product , stereochemistry , ketone , organic chemistry , medicinal chemistry , catalysis
Abstract The total syntheses of the natural product 3‐ O ‐methylfunicone ( 1 ), a member of the funicone class of compounds, and its derivatives is reported. The key reactions in the construction of the biaryl ketone core are a regioselective TMPZnCl · LiCl halogenation and a carbonylative Stille cross‐coupling reaction. In addition, the inhibitory activities of the funicones against Y‐family DNA polymerase κ (pol κ) and polymerase η (pol η) were determined. We found that 1 and 12 exhibit inhibitory activity against pol η and 1 also against pol κ.