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Total Synthesis of Alanense A through an Intramolecular Friedel–Crafts Alkylation

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https://figshare.com/articles/dataset/Total_Synthesis_of_Alanense_A_through_an_Intramolecular_Friedel_Crafts_Alkylation/25029472
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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·H2O 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.
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2024-01-19
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