A short linear synthesis culminating in a tandem addition/Prins/Friedel-Crafts/dehydration reaction affording 2,2,4-trisubstituted-4-dihydro-1H-benzo[f]isochromenes starting with phenylacetaldehyde and trimethylsilylacetylene has been developed. The target molecules are synthesized by a coupling of a homopropargylic alcohol and aldehyde in the presence of a stoichiometric amount of Lewis acid.  Variations in catalyst and protecting groups on yields and reaction control have been investigated. Additionally, variability at the 8 and 10 positions has been introduced through modification of the starting materials. 

Tandem addition/Prins/Friedel-Crafts/dehydration reactions towards 2,2,4-trisubstituted-2,4-dihydro-1H-benzo[<i>f</i>]isochromenes

244th National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.

Tandem addition/Prins/Friedel-Crafts/dehydration reactions towards 2,2,4-trisubstituted-2,4-dihydro-1H-benzo[f]isochromenes