Sassafras oil, carrot bits and microwaves: green lessons learned from the formal total synthesis of (−)-talampanel

Abstract

A formal total synthesis of (−)-talampanel (1), a 2,3-benzodiazepine is described. This work was undertaken to utilize greener reaction conditions.

From traditional to greener alternatives: potential of plant resources as a biotransformation tool in organic synthesis

“…13), which helped in ascertaining the stereochemistry of the benzyl group in the final product. 105 Similarly, Omori et al 106 and Yadav et al , 107 in their total synthesis of (−)-talampanel and R -(−) denopamine respectively, used carrot roots to highly enantioselectively yield alcohols 76 & 78 (Fig. 13).…”

A Highly Regioselective and Practical Synthesis of α‐Aryl Ketones under a Cooperative Cascade Effect of an Ionic Liquid and Tetrabutylammonium Fluoride

“…We were fascinated by the highly regioselective conversion of indene and dihydronapthalene halohydrins into 2‐indanone and 2‐tetralone respectively (Table , entries 5–6) in good yield. Interestingly piperonyl methyl ketone (Table , entry 1) and 2‐indanone (Table , entry 5) which are an important intermediate for various drugs including talampanel, fendosal respectively were also obtained by our protocol. However, the bromohydrin of electron withdrawing chloro substituted phenylpropene was found to be unstable hence they could not be used for the rearrangement reaction (Table , entry 7).…”