Bulletin of the Chemical Society of Japan · 1972 · 22 citations · 8 references
Life SciencesBotanyPlant SciencesMycologyPlant BiochemistryPlant PhysiologyPlant ProductsPlant-pathogen InteractionsPlant-pathogenic FungiTerpenoid BiosynthesisChemical CharacterizationDiterpene BiosynthesisPlant Defense CompoundsPlant Defense MetabolitesSesquiterpene BiosynthesisTerpene Compounds
Abstract The structure and configuration of rishitinol (2), isolated from tuber tissues of white potatoes (Solanum tuberlosum × S. demissum) infected by an incompatible race of Phytophtora infestans, were deduced from spectral and chemical data and confirmed by the synthesis of its recemate. 5,8-Dimethyl-1-tetralone-3-carboxylic acid (13) prepared from 2,5-dimethylbenzyl chloride was esterified, reduced, and then dehydrated to the dihydronaphthalene derivative (20), which was converted into the oxyisopropyl derivative (21). The hydroboration of 21 followed by hydrogen peroxide oxidation afforded a multi-component mixture, from which dl-rishitinol (25=dl-2) was isolated along with isomeric glycols (22–24).
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