Alternative synthesis of (+/-) cherylline dimethyl ether

Abstract

An alternative synthesis of isoquinoline alkaloid (+/-) cherylline dimethyl ether is reported. The steps involved are acid-catalyzed Michael addition of veratrole to p-methoxycinnamic acid, Curtius rearrangement, reduction of isocyanate intermediate followed by Pictet-Spangler cyclization.

Modular Approach to 9-Monosubstituted Fluorene Derivatives Using MoV Reagents

“…Depending on the desired substituent in position 9 of the fluorene (see Table ), either a Knoevenagel–Doebner condensation (route A) or a Horner–Wadsworth–Emmons reaction (route B) was performed in high yield (89–99%) . Subsequently, an acid catalyzed 1,4-addition of veratrole and then esterification of the acid moieties were carried out to obtain diaryl propionates 6 , diaryl propionitriles 7 , and diaryl propionic amides 8 …”

Amaryllidaceae and Sceletium alkaloids

“…An efficient synthesis of (AE)-cherylline dimethyl ether 182 has been completed. 113 The synthetic sequence included trifluoroacetic acid-mediated Michael addition of anisole to pmethoxycinnamic acid, a Curtius degradation, and Pictet-Spengler ring annulations.…”