473827-36-0Relevant academic research and scientific papers
A facile synthesis of natural products chaetomellic acid A and 1,7(Z)-nonadecadiene-2,3-dicarboxylic acid
Kar, Anirban,Argade, Narshinha P.
, p. 7131 - 7134 (2002)
Synthesis of recently isolated bioactive natural products chaetomellic acid A anhydride (1) and a novel 1,7- (Z)-nonadecadiene-2,3-dicarboxylic acid (2) have been described. Chemoselective carbon-carbon SN2′ coupling reactions of appropriate Grignard reagents with dimethyl bromomethylfumarate (7) in diethyl ether in the presence of HMPA at room temperature furnished the corresponding diesters 8 and 15 in 60-62% yields. The formed diesters 8 and 15 on hydrolysis gave respectively the corresponding desired diacids 9 and 2 in quantitative yields. Acetic anhydride induced ring closure of diacids 9 and 2 respectively gave the chaetomellic acid A anhydride (1) and isochaetomellic acid B anhydride (16) with 38-39% overall yields in five steps.
