The Synthesis of Hydronaphthalenes from m-Toluic Acid via Cyclization of Thioacetal Monosulfoxides |
| |
Authors: | James A Marshall Peter G M Wuts |
| |
Institution: | Department of Chemistry , Northwestern University , Evanston, Illinois, 60201 |
| |
Abstract: | We recently developed a convenient route to hexahydronaphthalenols such as 5 (R=CO2CH3 or CH3) starting from m-toluic acid (1)1. The key features of the route involved reduction-alkylation of the toluic acid to the dihydro derivative 2 2, subsequent deprotection and oxidation of the side chain primary alcohol, and acid-catalyzed cyclization of the resulting aldehyde 4. In the case of the dimethylnaphthalenols 5 (R=CH3), conversion of the angular carboxylic function to the methyl group was effected prior to cyclization via reduction of the p-toluenesulfonic ester of the neopentyl alcohol 3 (R=CH2OH) using lithium triethylborohydride3. |
| |
Keywords: | |
|
|