Chaetomellic Acid A and 1,7(Z)- Nonadecadiene-2,3-dicarboxylic Acid
Abstract
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.
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