terpestacin and cyclopentanone

A stereocontrolled total synthesis of (-)-terpestacin has been achieved starting from (R)-(-)-carvone as a chiral pool and (E,E)-farnesol via a highly convergent approach. Thus, (R)-(-)-carvone was transformed into the cyclopentanone segment through a series of high yielding operations with the proper setup of all the stereochemical centers while (E,E)-farnesol was converted into the other requisite building block via a series of high yielding reactions. The cyclopentanone intermediate was both selectively enolized and alkylated at room temperature to yield the desired coupling product, which provided the natural product upon further transformations.

Topics: Alkylation; Ascomycota; Biological Products; Bridged Bicyclo Compounds; Cyclohexane Monoterpenes; Cyclopentanes; Farnesol; Monoterpenes; Stereoisomerism