Last fight….

…..within february and march 2012 I really got very close to the total synthesis of my target molecule. I had to run through three synthetic strategies regarding the last steps. Changing the functional groups implemented in the precursor should give me the final product. Unfortunately it was not possible to isolate the natural product in the end, although I could already detect the molecular mass in LC-MS and HRMS-ESI already. I had a crude product mixture in hands which I could not purify neither by simple column chromatography nor by more advanced HPL-Chromatography. On the other hand my results are valuable as I could develop a dependable strategy to build up necessary precursors.
Hopefully at some point people will make use of my laboratory experience and my results so far. In my opinion the synthetic strategy I was following is superior to other strategies I found so far. With my reactions I can more or less easily provdide precursors in a convergent fashion.

What my synthesis was about, I will tell you in some more detailed posts.

Stay tuned 🙂
Kaeptn Future


LC-MS check, column chromatography, HRMS check

Today I did it!

The hydrolysis of a very stable diethyl-acetal with 2M hydrogenchloride worked (THF, 2 h, reflux) and the following intramolecular cyclisation of a beta-ketoamide with the now deprotected aldehyde worked as well. LC-MS reactioncontroll is a really helpfull tool to get quick information about a conversion. I proceeded to check wether the compund is TLC stable or not by simple 2D-TLC. Yes! It is! Quickly ran a column with HRMS-analysis of the collected Spot. Perfect! It´s a mixture of three compounds with nearly the same Rf-value ! The cyclised compound, the cyclised compound including elimination of the newly formed alcohol and traces of my final compound! Tomorrow I will give sodiumhydroxide another chance to give me the cyclised and eliminated compound.  Then it is just one step away from the total synthesis of…..

I just want you to participate in this progress and I want to show, how emotional chemistry can be. More details regarding the synthesis strategy and the final product will follow as soon as possible.


Stay tuned 😉