Spanish chemists have completed the stereospecific total synthesis of (+)-myrrhanol C.
(+)-Myrrhanol C is a natural triterpene isolated from mastic gum (the resin of Pistacia lentiscus), a substance well known for its medicinal properties as well as use in various cuisines. The compound itself was used to embalm corpses in ancient Egypt. More recently, it has been recognised as a promising anti-prostate cancer lead. However, before a molecule can be used to develop drugs, a successful synthesis must be developed.
Mastic gum (from Pistacia lentiscus, pictured) has been used for many applications, from treating snakebites to tooth whiteners. © Science Photo Library
Alejandro Barrero and his group at the University of Granada have done just that. Their synthesis starts with (–)-sclareol, a bicyclic diterpene alcohol isolated from clary sage (Salvia sclarea). It then proceeds through a key C–H oxidation step, which is achieved with cytochrome P450 enzyme catalysis by incubating a reaction intermediate with the fungus Mucor plumbeus.
By cultivating clary sage, Barrero can sustainably produce (–)-sclareol, meaning (+)-myrrhanol C can be made on a large scale that is also environmentally friendly.
Read the full story in Chemistry World
And read the OBC paper, highlighted as being HOT by the referees, for free here:
First synthesis of (+)-myrrhanol C, an anti-prostate cancer lead
Victoriano Domingo, Lidia Lorenzo, José F. Quilez del Moral and Alejandro F. Barrero
DOI: 10.1039/C2OB26947C
