Enantiospecific syntheses of paeonilactone A, paeonilactone B, 7S-paeonimetabolin-I, and 7R-paeonimetabolin-I from R-(−)-carvone

Enantioselective synthesis of (−)-paeonilide

“…[5][6][7] Since Peony roots are under phytochemical investigation for many years, several new monoterpenoids could be isolated, characterized and pharmacologically analyzed ( Figure 1): [8][9] Figure 1: Examples of natural products isolated from peony roots.…”

“…Paeonia root bark containing prescriptions like the multiherbal formula GuiZhiFuLing-Wan are employed in China, Japan and Korea to alleviate the syndromes of blood stasis and stiffness of abdominal muscles. [1][2][3] (+)-Paeonilide (+)-( 1), a monoterpenoid isolated from Paeonia delavayi, 4 is a substructure of the privileged class of ginkgolides. In bioassays it showed selective inhibition of the platelet aggregation induced by PAF (platelet activating factor) with an IC 50 value of 8 mg mL À1 , but importantly, no effect on the platelet aggregation induced by adenoside diphosphate (ADP) or arachidonic acid (AA).…”

Total Synthesis of (±)-Paeonilide

“…Paeonia root bark is used in traditional Chinese medicine for treatment of abdominal pain and syndromes such as stiffness of abdominal muscles . Phytochemical research has generated a number of structurally related monoterpenes from paeony roots .…”

An Enantioselective Route to Paeonilactone A via Palladium- and Copper-Catalyzed Reactions

“…Paeonilactone A ( 1 ), B ( 2 ), and C ( 3 ) (Figure ) are some of the compounds isolated from paeony root, the root of Paeonia Albiflora Pallas . This root has been extensively used in Chinese and Japanese herbal medicine for treatment of abdominal pain and syndromes such as stiffness of abdominal muscles . Moreover, paeonilactone C has been proven to suppress both directly and indirectly stimulated muscle twitching of sciatic nerve−sartorius muscle preparations from frogs .…”

“…Moreover, paeonilactone C has been proven to suppress both directly and indirectly stimulated muscle twitching of sciatic nerve−sartorius muscle preparations from frogs . Several synthetic approaches toward paeonilactones have been published in racemic 3 as well as enantioselective ,, forms. However, all of the enantioselective routes used a chiral pool approach.…”