Peter, Aron; Crisenza, Giacomo E. M.; Procter, David J. published the artcile< Asymmetric Total Synthesis of (-)-Phaeocaulisin A>, Formula: C19H34O2, the main research area is asym total synthesis phaeocaulisin A samarium iodide cyclization lactone.
The therapeutic properties of Curcuma (ginger and turmeric’s family) have long been known in traditional medicine. However, only recently have guaiane-type sesquiterpenes extracted from Curcuma phaeocaulis been submitted to biol. testing, and their enhanced bioactivity was highlighted. Among these compounds, phaeocaulisin A has shown remarkable anti-inflammatory and anticancer activity, which appears to be tied to the unique bridged acetal moiety embedded in its tetracyclic framework. Prompted by the promising biol. profile of phaeocaulisin A and by the absence of a synthetic route for its provision, we have implemented the first enantioselective total synthesis of phaeocaulisin A in 17 steps with 2% overall yield. Our route design builds on the identification of an enantioenriched lactone intermediate, tailored with both a ketone moiety and a conjugated alkene system. Taking advantage of the umpolung carbonyl-olefin coupling reactivity enabled by the archetypal single-electron transfer (SET) reductant samarium diiodide (SmI2), the lactone intermediate was submitted to two sequential SmI2-mediated cyclizations to stereoselectively construct the polycyclic core of the natural product. Crucially, by exploiting the innate inner-sphere nature of carbonyl reduction using SmI2, we have used a steric blocking strategy to render sites SET-unreceptive and thus achieve chemoselective reduction in a complex substrate. Our asym. route enabled elucidation of the naturally occurring isomer of phaeocaulisin A and provides a synthetic platform to access other guaiane-type sesquiterpenes from C. phaeocaulis-as well as their synthetic derivatives-for medicinal chem. and drug design.
Journal of the American Chemical Society published new progress about Absolute configuration (absolute configuration reassignment of natural phaeocaulisin A). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Formula: C19H34O2.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics