The Synaptic Leap

I've been working for six weeks now with the Todd Research Group at Sydney University as part of an undergraduate summer research program. The aim of my project is to synthesise analogues of this group of hits from the  antimalarial dataset released by GSK. They are referred to here as 'near neighbours' because they share the arylpyrrole moiety present in the two hits (TCMDC 123812 and 123794) Paul has been working on, but have a thiazolodinone side chain. The major components of my project are:

January 2012, Here’s a quick update on where we are regards the Bronsted Acid catalysed Pictet-Spengler reaction.
 

We have received encouraging biological results for the analogues we sent for testing before Christmas. Mat has discussed this here on TSL and on G+. Our best hit came from the "near-neighbour" compound and the original GSK hits came out slightly less active than in their original high throughput screen. However, Paul Willis at MMV rates TCMDC-123794 as a better lead than PMY 14-1 (TSL post).

It’s been too long since I’ve updated the progress of this project on here but here’s a brief summary of where we are and what’s planned for the near future.  From late November we’ve had a summer student, Kat Badiola, working on the project.  She started with preparing pure, racemic samples of the 3 PZQ analogues shown below (compounds 6-8) via the Pictet-Spengler cyc

I was looking at all the difficulty that is occuring with finding a cheap source of chiral catalyst for the Pictet-Splenger and mused about using Phenylglycine, as this avoids the issue due to it being part of the chiral pool.
Anyway here is my attempt at getting the key ring system together for the system. Don't think anything I used is particularly expensive. Sorry about the conditions being vague, was just a quick thought that I came up with.