Abstract
The first chemical synthesis of S2502 and S2507, highly active antiviral, bioengineered fermentation products, has been achieved using a biomimetic approach. Key steps of the synthesis involved addition of the dianion of acetylacetone to isochromene 10 , followed by boron tribromide mediated simultaneous methyl ether cleavage, E /Z isomerization, cyclization, and transesterification/saponification to give S2502 (7 ) and S2507 (8 ). In a related reaction, the analogous esters 20 and 21 were obtained by treatment of isochromene 10 with the dianion of methyl acetoacetate, followed by boron tribromide treatment.
Key words
antiviral compounds - dianion condensation - biomimetic synthesis - boron tribromide -
E /Z -isomerization
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