One of the largest subfamilies within the famous Daphniphyllum alkaloid family is made up of the yuzurimine-type(or macrodaphniphyllamine-type) alkaloids. Their complex aza-polycyclic caged structures, several contigu...One of the largest subfamilies within the famous Daphniphyllum alkaloid family is made up of the yuzurimine-type(or macrodaphniphyllamine-type) alkaloids. Their complex aza-polycyclic caged structures, several contiguous stereogenic centers, and vicinal all-carbon quaternary centers make these alkaloids formidable challenge for synthetic chemists. Recently, synthesis of these alkaloids has received extensive attention from our community. Herein, we wish to report the total synthesis of C_(14)–epideoxycalyciphylline H, a putative member of yuzurimine-type alkaloid subfamily. Key transformations employed in our approach include an intramolecular Prins reaction and a Pd-catalyzed enyne cycloisomerization. In addition, synthesis of a daphnezomine L-type alkaloid, paxdaphnidine A, was also studied.展开更多
An efficient and straightforward synthesis ofberaprost sodium was developed with dicyclopentadiene as a starting material, a one-pot reaction product 5 as key intermediate and the Prins reaction and the Homer-Wadswort...An efficient and straightforward synthesis ofberaprost sodium was developed with dicyclopentadiene as a starting material, a one-pot reaction product 5 as key intermediate and the Prins reaction and the Homer-Wadsworth-Emmons reaction as key steps. The structures of the key intermediate and the target compound were confirmed by 1H NMR, 13C NMR and MS. The purity of beraprost sodium identified by high performance liquid chromatography（HPLC） was identical to that of Japanese Pharmacopoeia（16th）. This development will be used for the industrial synthesis of beraprost sodium.展开更多
基金the National Natural Science Foundation of China (Nos.21971104 and 22271136)Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis (No.ZDSYS20190902093215877)+4 种基金Guangdong Provincial Key Laboratory of Catalysis (No.2020B121201002)Guangdong Innovative Program (No.2019BT02Y335)Education Department of Guangdong Province, Key research projects in colleges and universities in Guangdong Province (No.2021ZDZX2035)Shenzhen Nobel Prize Scientists Laboratory Project (No.C17783101)Innovative Team of Universities in Guangdong Province (No.2020KCXTD016)。
文摘One of the largest subfamilies within the famous Daphniphyllum alkaloid family is made up of the yuzurimine-type(or macrodaphniphyllamine-type) alkaloids. Their complex aza-polycyclic caged structures, several contiguous stereogenic centers, and vicinal all-carbon quaternary centers make these alkaloids formidable challenge for synthetic chemists. Recently, synthesis of these alkaloids has received extensive attention from our community. Herein, we wish to report the total synthesis of C_(14)–epideoxycalyciphylline H, a putative member of yuzurimine-type alkaloid subfamily. Key transformations employed in our approach include an intramolecular Prins reaction and a Pd-catalyzed enyne cycloisomerization. In addition, synthesis of a daphnezomine L-type alkaloid, paxdaphnidine A, was also studied.
文摘An efficient and straightforward synthesis ofberaprost sodium was developed with dicyclopentadiene as a starting material, a one-pot reaction product 5 as key intermediate and the Prins reaction and the Homer-Wadsworth-Emmons reaction as key steps. The structures of the key intermediate and the target compound were confirmed by 1H NMR, 13C NMR and MS. The purity of beraprost sodium identified by high performance liquid chromatography（HPLC） was identical to that of Japanese Pharmacopoeia（16th）. This development will be used for the industrial synthesis of beraprost sodium.
