A new type of spirocyclic bisoxindole-based
C2-symmetric
diols (SBIDOLs) was designed and synthesized. A series of racemic
SBIDOL derivatives (6a–6g) were readily synthesized
from commercially available 2-halo-5-methoxyanilines 1 (X = Cl or Br) through N-mono alkylation, acylation, oxidation,
double intramolecular Friedel–Crafts reaction, and demethylation
reactions. The optical resolution of racemic 6b was achieved
via fractional crystallization of their bis-l-menthoxycarboxylates.
Further modifications of SBIDOLs were investigated, leading to 5,5′-diaryl
SBIDOL derivatives (11a and 11b) through
Pd-catalyzed Suzuki coupling and DM-SBIDOL 12 by Pd/C-catalyzed
hydrogenative dechlorination reactions.