Total synthesis and absolute stereostructure of (+)-dysideapalaunic acid
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- Vol. 22 (8) , 1803-1807
- https://doi.org/10.1039/p19910001803
Abstract
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-(4methylpent-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).Keywords
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