Divergent total syntheses of isobatzellines A/B and batzelline A were accomplished. A fully substituted common indole intermediate bearing C-2 methylthio and C-5 chloro groups was constructed via ring expansion of benzocyclobutenone oxime sulfonate with NaSMe and a benzyne-mediated cyclization/functionalization sequence as the key steps. The total synthesis of isobatzelline B was achieved via formation of the iminoquinone structure by the redox-neutral acid-promoted C-5 proto-dechlorination of the common indole intermediate. The total syntheses of isobatzelline A and batzelline A were completed in a divergent manner by oxidation of the common indole intermediate using MnO2 or Mn(OAc)3, respectively.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry