Expeditious Synthesis of Isoquinolones and Isocoumarins with a Vinyl Borane as an Acetylene Equivalent

European J Org Chem. 2016 Aug;2016(24):4171-4175. doi: 10.1002/ejoc.201600575. Epub 2016 Jul 26.

Abstract

An innovative and simple expeditious synthesis of 3,4-unsubstituted isoquinolones and isocoumarins starting from safe and easy to handle two-carbon acetylene equivalent was developed. The synthetic potential of this new method was further demonstrated in the facile total synthesis of two naturally occurring alkaloids: corydaldine and doryanine.

Keywords: Suzuki coupling; boronate; isocoumarin; isoquinolone; vinyl ether.