Total Synthesis Blog

Today (time to writing posts – at leats!) – some quite simple-looking target: 3-hydroxypipecolic acid. The structure of this target is drawn below (just click on image and enjoy new system of showing pictures on this blog ):

As you can see – it really doesn’t look terrible: two stereocentres and only one ring. It’s hard to believe that only several approaches to such system was developed (authors of paper claim: only four approaches). Let’s say something about biological properties of (2S,3R)-3-hydroxypipecolic acid… Well, structural feature of 3-hydroxypipecolic acid is preasent in many natural and non-natural compounds, for example tetrazomine which was isolated from Saccharothrix mutabilis and exhibiting antitumor activity (3-hydroxypipecolic acid subunit is marked):

The retrosynthesis of (2S,3R)-3-hydroxypipecolic acid is shown below:

Read the rest of this entry »

Today, some target which seems to be quite easy to synthesise – (-)-Andrachcinidine:

That 2,6-disubstituted piperidine-derived alkaloid was isolated from plant Andrachne aspera (picture taken from http://www.teline.fr/:

Yes… target seems to be easy to synthesise, but its synthesis is quite complicated. Retrosynthesis of (-)-andrachcinidine is shown below:

Read the rest of this entry »