Total Synthesis Blog

Today, total synthesis of hyptolide which was published in Tetrahedron Letters. Structure of target molecule is drawn below (click on images to enlarge them ):

Authors wrote about some “important biological activities” and “interesting pharmacological properties” and they wrote nothing more So, what do we have here? Well, four stereocentres, two double bonds and α,β-unsaturated δ-lactone ring makes hyptolide really nice target molecule.

Hyptolide is present in plants from family called Lamiaceae, especially in genera Hyptis and Syncolostemon. There are several compounds related to hyptolide: spicigerolide, anamarine and synrotolide. Their are shown below.

I’ve tried to plan the synthesis of hyptolide and my proposition of retrosynthesis is presented at next images.

I hope that everything is clear (P means some protecting groups)

The real retrosynthesis of hyptolide:
Read the rest of this entry »

This time short synthesis of racemic Cacalol:

This is a sesquiterpene isolated from the roots of Psacalium decompositum and it exhibit some interesting biological properties including antihyperglycemic, anti-inflammatory, antimicrobial and antioxidant activities. Authors of paper didn’t mention anything about biological activity of single enantiomers of Cacalol.

Retrosynthesis chart (not very good-looking…) is shown below:
Read the rest of this entry »