Total Synthesis of Alanense A through an Intramolecular Friedel–Crafts Alkylation
Kosho Makino, Rio Fukuda, Shunsuke Sueki, Masahiro Anada
Abstract
The first total synthesis of cadinane sesquiterpenoid alanense A, in which an intramolecular dehydrative Friedel–Crafts alkylation of 2,5-diaryl-2-pentanol is incorporated as a key step, has been achieved. The combinatorial use of p -TsOH·H 2 O as a catalyst and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as a solvent provides 1,1-disubstituted tetrahydronaphthalene in 97% yield. It was also found that the combination of p -TsOH and HFIP is effective for the removal of phenolic MOM ether.
Topics & Concepts
ChemistryFriedel–Crafts reactionIntramolecular forceAlkylationYield (engineering)Total synthesisSolventCatalysisEtherOrganic chemistryMedicinal chemistryCombinatorial chemistryMaterials scienceMetallurgySynthetic Organic Chemistry MethodsAsymmetric Synthesis and CatalysisPlant-derived Lignans Synthesis and Bioactivity