posted on 2024-01-19, 16:37authored byKosho Makino, Rio Fukuda, Shunsuke Sueki, Masahiro Anada
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.