Total Synthesis of Clostrienose

This paper considers the total synthesis of a cellular differentiation regulator of Clostridium acetobutylicum, clostrienose, which is a unique fatty-acid glycosyl ester consisting of clostrienoic acid, (3R,5E,8E,10E)-3-hydroxy-tetradeca-5,8,10-trienoic acid and a-D-galactofuranosyl-(1? 2)-a-L-rhamnose. The key features of our synthesis include stereoselective construction of a skipped-triene system in clostrienoic acid and its esterification with a disaccharide residue. The partially protected clostrienoic acid employed for the coupling also served for the preparation of L-rhamnosyl clostrienoate, thus leading to confirmation of the proposed structure unambiguously.

Automated summary

This paper discusses the total synthesis of clostrienose, a cellular differentiation regulator from Clostridium acetobutylicum. The synthesis involves stereoselective construction of a skipped-triene system in clostrienoic acid and its subsequent esterification with a disaccharide residue. The partially protected clostrienoic acid used for the coupling reaction is also employed for the preparation of L-rhamnosyl clostrienoate, providing unambiguous confirmation of the proposed structure.