Beilstein J. Org. Chem.2009,5, No. 80, doi:10.3762/bjoc.5.80
Sciences and Humanities Department, SVNIT, Surat – 395 007, India 10.3762/bjoc.5.80 Abstract A synthesis of (±)-cherylline dimethyl ether is reported. The key steps involved are Michael-type addition, radicalazidonation of an aldehyde, Curtius rearrangement, and reduction of an isocyanate intermediate
followed by Pictet–Spengler cyclization.
Keywords: Curtius rearrangement; Michael reaction; Pictet–Spengler cyclization; radicalazidonation; Introduction
Aryl-1,2,3,4-tetrahydroisoquinolines have attracted much attention from the synthetic community owing to the potential biological activities of this
are Michael addition, radicalazidonation of aldehydes [18], Curtius rearrangement, and reduction of an isocyanate intermediate followed by Pictet–Spengler cyclization.
Results and Discussion
Our retrosynthetic analysis of (±)-cherylline dimethyl ether (5) is depicted in Scheme 1. It can be