Synthesis of novel mast cell-stabilising and anti-allergic 1,2,3,4-tetrahydro-1-naphthalenols and related compounds

In a continuation of our studies into indan and tetralin systems as novel modulators of allergic and inflammatory phenomena, we have extended our work to include dimers linked via C–C bonds. Of these compounds, 2-Benzyl-2-[2-phenyl-1-ethenyl]-1,2,3,4-tetrahydro-1-naphthalenol 12 exhibited most promising activity both in vitro and in vivo.

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► Novel compounds obtained via the SnCl4-catalysed Mukaiyama coupling of silyl enol ethers and acetals.
► Compounds tested in vitro and in vivo in anti-allergic models.
► Less strained analogues less active than those bearing either an indenyl or dihydronaphthalenyl fragment.
► Anti-inflammatory activity was not linked to mast cell-stabilising activity.