122934-76-3Relevant academic research and scientific papers
Total Synthesis of (+)-Dysideapalaunic Acid
Hagiwara, Hisahiro,Uda, Hisashi
, p. 815 - 817 (1988)
The total synthesis of (+)-dysideapalaunic acid (1), a sesquiterpenic aldose reductase inhibitor, has been accomplished; the absolute stereochemistry of (1) is thus established as 4S,5S,10S.
Total Synthesis and Absolute Stereostructure of (+)-Dysideapalaunic Acid
Hagiwara, Hisahiro,Uda, Hisashi
, p. 1803 - 1807 (2007/10/02)
The total synthesis of (+)-dysideapalaunic acid, a sesterterpenic aldose reductase inhibitor, has been accomplished.Starting from optically active (8aS)-(+)-3,4,8,8a-tetrahydro-5,8a-dimethylnaphthalene-1,6(2H,7H)-dione, (5S)-(-)-3,4,4a,5,6,7,8,8a-octahydro-5,8a-dimethyl-5-(4-methylpent-3-enyl)naphthalen-1(2H)-one ethylene acetal has been synthesized in eight steps involving reductive allylation, deoxygenation, and a Wittig condensation.Transformation of this ethylene acetal via methylation at C-2, Grignard addition, and a Horner-Emmons reaction furnished the required (+)-acid in eight steps.Thus, the absolute stereochemistry of the (+)-acid has been established as (4aS,5S,8aS).
