gem-Dibromomethylarenes as Aldehyde Surrogates in the Pictet-Spengler Synthesis of Tetrahydroisoquinolines and Isoindoloisoquinolones

摘要

A new variant of the Pictet-Spengler reaction has been developed using gem-dibromomethylarenes as aldehyde surrogates to afford a variety of tetrahydroisoquinoline and isoindoloisoqui-nolone ring systems in good yields. These systems comprise important motifs in naturally occurring bioactive substances.Isoquinoline alkaloids constitute a large family of natural products that exhibit a broad range of biological activities.1 Among the members of this class of compounds, tetrahydroisoquinoline derivatives comprise a major group. Many of them display important biological activities, and possess for example, anti-inflammatory, anti-microbial, anti-leukemic and anti-tumor properties,2 which has promoted the development of a number of synthetic methodologies for the construction of the tetrahydroisoquinoline nucleus.