How do you think about organic synthesis?

As a good chemist you will consider every retrosynthetic cut very carefully. As you don´t only strive to make your target molecule smaller but also to reduce its complexity you will always look for the most powerful transformation.

But what would happen if you wouldn´t do that? By just using simple cuts (e.g. next to heteroatoms and through double bonds) you should end up with a small but complex precursor!

So why not build up this small precursor from C1-fragments, just like you would build a molecular model?

Ch Matteson Narrow

For this we want to use and continue to develop the diastereoselective homologation of chiral boronates first introduced by D. Matteson. This chemistry allows you to “grow” a chiral alkyl boronate (1) via a halide intermediate (2) into a substituted homologue (3), which can then be reused for further homologations or the full array of boron-based transformations.

With this chemistry we target important natural and unnatural products. Pushing against its current limitations we are always on the lookout for the ultimate modular synthesis as well as new methods for more facile applications as well as possibilities for future automation.

 

Never heard about Matteson Homologations?

Here is a video that introduces the reaction (2 min) and explains the mechanism (15 min):

Application in Synthesis

Our synthesis of Cytisine puts the Matteson Reaction at the very front of the sequence: