Diversity-Oriented Approach to Cyclophanes via Fischer Indolization and Ring-Closing Metathesis: Substrate-Controlled Stereochemical Outcome in RCM

Here, we report a new and diversity-oriented
approach to macrocyclic
cyclophanes by a Grignard reaction, followed by Fischer indolization
and ring-closing metathesis (RCM) as key steps. The configuration
of the double bond formed during the RCM depends upon the order of
synthetic sequence used. Fischer indolization followed by RCM delivers
the cis isomer, whereas RCM followed by Fischer indolization gives
the trans isomer.