Synthesis of propellanes containing a bicyclo[2.2.2]octene unit via the Diels-Alder reaction and ring-closing metathesis as key steps

Sambasivarao Kotha; Sunil Pulletikurti

doi:10.1039/c8ra02687d

Synthesis of propellanes containing a bicyclo[2.2.2]octene unit via the Diels-Alder reaction and ring-closing metathesis as key steps

RSC Adv. 2018 Apr 19;8(27):14906-14915. doi: 10.1039/c8ra02687d. eCollection 2018 Apr 18.

Authors

Sambasivarao Kotha¹, Sunil Pulletikurti¹

Affiliation

¹ Department of Chemistry, Indian Institute of Technology-Bombay Powai Mumbai-400 076 India srk@chem.iitb.ac.in.

Abstract

The synthesis of propellanes containing bicyclo[2.2.2]octene via olefin metathesis approach is less explored. Herein, we describe a simple and convenient method to synthesize propellane derivatives containing a bicyclo[2.2.2]octene unit which are structurally similar to 11β-HSD1 inhibitors by sequential usage of the Diels-Alder reaction, C-allylation and ring-closing metathesis (RCM) as the key steps. Additionally, we expanded this approach to an endo-tricyclo[4.2.2.0^2,5]decene derivative which is a useful monomer for polymer synthesis and we have also synthesized basketene and anthracene-based propellanes using the same strategy.