Ajay Kumar Chinnam

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.

Hybrid macrocycle formation and spiro annulation on cis-syn-cis-tricyclo[6.3.0.02,6]undeca-3,11-dione and its congeners via ring-closing metathesis

Summary We have developed a simple methodology to transform cis-syn-cis-triquinane derivative 2 into the diindole based macrocycle 6 involving Fischer indolization and ring-closing metathesis (RCM). Various spiro-polyquinane derivatives have been assembled via RCM as a key step.

Design and synthesis of hybrid cyclophanes containing thiophene and indole units via Grignard reaction, Fischer indolization and ring-closing metathesis as key steps.

Summary We demonstrate a new synthetic strategy to cyclophanes containing thiophene and indole moieties via Grignard addition, Fischer indolization and ring-closing metathesis as key steps.

Synthesis of indole-based propellane derivatives via Weiss-Cook condensation, Fischer indole cyclization, and ring-closing metathesis as key steps.

Summary A variety of highly functionalized indole-based [n.3.3]propellane derivatives is described. The synthesis of the propellane derivatives involves a Weiss–Cook condensation, a Fischer indole cyclization, and a ring-closing metathesis as key steps.