02115nas a2200217   4500008004100000022001400041245016000055210006900215260000900284490000700293520129800300653001701598653002101615653001601636653002601652653001701678100001901695700002701714700003101741856012501772       2023                        eng d  a1861-472800aLate-stage C(sp(2))-H arylation of artemisinic acid and arteannuin B: effect of olefin migration towards synthesis of C-13 arylated artemisinin derivatives0 aLatestage Csp2H arylation of artemisinic acid and arteannuin B e  cAPR 0 v183 a<p>In recent years, C-H bond functionalization has emerged as a pivotal tool for late-stage functionalization of complex natural products for the synthesis of potent biologically active derivatives. Artemisinin and its C-12 functionalized semi-synthetic derivatives are well-known clinically used anti-malarial drugs due to the presence of the essential 1,2,4-trioxane pharmacophore. However, in the wake of parasite developing resistance against artemisinin-based drugs, we conceptualized the synthesis of C-13 functionalized artemisinin derivatives as new antimalarials. In this regard, we envisaged that artemisinic acid could be a suitable precursor for the synthesis of C-13 functionalized artemisinin derivatives. Herein, we report C-13 arylation of artemisinic acid, a sesquiterpene acid and our attempts towards synthesis of C-13 arylated artemisinin derivatives. However, all our efforts resulted in the formation of a novel ring-contracted rearranged product. Additionally, we have extended our developed protocol for C-13 arylation of arteannuin B, a sesquiterpene lactone epoxide considered to be the biogenetic precursor of artemisinic acid. Indeed, the synthesis of C-13 arylated arteannuin B renders our developed protocol to be effective in sesquiterpene lactone as well.</p>
10aArteannuin B10aArtemisinic acid10aartemisinin10aC-H functionalization10aPd-catalysis1 aPaul, Sayantan1 aGhodake, Balaji, M. M.1 aBhattacharya, Asish, K. K.  uhttps://library.ncl.res.in/content/late-stage-csp2-h-arylation-artemisinic-acid-and-arteannuin-b-effect-olefin-migration