Asymmetric total synthesis and antidepressant activity of (-)-sila-mesembranol bearing a silicon stereocenter

Asymmetric total synthesis of (-)-sila-mesembranol, the silicon analog of the natural alkaloid (-)-mesembranol has been achieved in 3.3% yield over 11 steps. The chiral silicon center was enantioselectively constructed via the asymmetric expansion of a silacyclobutane ring. The synthetic (-)-sila-mesembranol in mice exhibits better antidepressant effects than its carbon counterpart.

Automated summary

The asymmetric total synthesis of (-)-sila-mesembranol, the silicon analog of (-)-mesembranol, was achieved in 3.3% yield over 11 steps. The chiral silicon center was enantioselectively constructed through the asymmetric expansion of a silacyclobutane ring. The synthetic (-)-sila-mesembranol exhibited better antidepressant effects in mice compared to its carbon counterpart.