Asymmetric Total Synthesis of (-)-(3 R)-Inthomycin C

Org Lett. 2018 Jun 15;20(12):3583-3586. doi: 10.1021/acs.orglett.8b01370. Epub 2018 Jun 4.

Abstract

A short (10 step) and efficient (15% overall yield) synthesis of the natural product (-)-(3 R)-inthomycin C is reported. The key steps comprise three C-C bond-forming reactions: (i) a vinylogous Mukaiyama aldol, (ii) an olefin cross-metathesis reaction, and (iii) an asymmetric Mukaiyama-Kiyooka aldol. This route is notable for its brevity and has the advantage of lacking stoichiometric tin-promoted cross-coupling reactions present in previous approaches. Initial investigations on the biological activity of (-)-(3 R)-inthomycin C and structural analogues on human cancer cell lines are also described for the first time.

Publication types

  • Research Support, Non-U.S. Gov't