Article
Chemistry, Organic
Katarina L. Keel, Jetze J. Tepe
Summary: The study presents the first total synthesis of Nortopsentin D, involving a pivotal condensation and subsequent cyclization of amidine and dione via a pinacol-like rearrangement. This unique synthetic strategy is significant for the formation of 5,5-disubstituted (4H)-imidazol-4-one containing natural products.
Article
Chemistry, Organic
Mervic D. Kagho, Helen Hintersatz, Andreas Ihle, Haoxuan Zeng, Hedda Schrey, Wera Colisi, Philipp Klahn, Marc Stadler, Clemens Bruhn, Tobias Rueffer, Heinrich Lang, Klaus Banert
Summary: The racemic total synthesis of nitrabirine and its epimer 2-epi nitrabirine was achieved via a six-step route involving biomimetic late-stage heterocyclization. Biological evaluation revealed biofilm dispersal effects against Candida albicans for both compounds, along with moderate antibacterial activities and potent cytotoxic activities for specific derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Emmanuel Cigan, Jakob Pletz, Sarah A. Berger, Bettina Hierzberger, Michael Grilec-Zlamal, Alexander Steiner, Isabel Oroz-Guinea, Wolfgang Kroutil
Summary: This study demonstrates an efficient access to the morphinan scaffold using a combination of organic synthesis and enzymatic reactions. The synthesis of a medicinally important compound class, promorphinans, was achieved by minimizing protecting group techniques and utilizing biocatalysis.
Article
Chemistry, Multidisciplinary
Emmanuel Cigan, Jakob Pletz, Sarah A. Berger, Bettina Hierzberger, Michael Grilec-Zlamal, Alexander Steiner, Isabel Oroz-Guinea, Wolfgang Kroutil
Summary: A biomimetic chemo-enzymatic strategy was demonstrated to efficiently synthesize the natural promorphinan intermediate (+)-salutaridine. This was achieved by combining organic synthesis and enzymatic transformations, resulting in high yields and enantioselectivities. This approach provides an unprecedented access to the medicinally important compound class of promorphinans.
Article
Multidisciplinary Sciences
Sangbin Park, Gyumin Kang, Chansu Kim, Dongwook Kim, Sunkyu Han
Summary: Securinega alkaloids have been a subject of interest in synthetic chemistry for a long time. This study presents a synthetic solution to accessing high-oxidation state securinega alkaloids by completing the total synthesis of various C4-oxygenated securinine-type alkaloids. The discoveries in this study offer a fundamental synthetic solution to all known securinine-type natural products and could be useful for systematic biological studies.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Gang Wang, Jin-Chen Li, Yong-Gui Zhou, Zhi-Shi Ye
Summary: This paper presents an enantioselective construction method for indole-fused bicyclo[3.2.1]octanes, utilizing a Heck-type reaction triggered by aminopalladition to achieve construction of an all-carbon quaternary bridgehead stereocenter, with mild conditions and good tolerance for various functional groups. The method can be scaled up to demonstrate practicality.
Article
Chemistry, Multidisciplinary
Qingdong Hu, Chang Guo
Summary: The synthesis of structurally diverse multiligated platinum complexes, characterized by X-ray crystallography, opens up new reaction space and enables faster screening. The Pt/Cu dual catalytic system shows new cooperative reactivity, leading to the asymmetric synthesis of valuable functionalized indoles with good yields and excellent enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Kelly E. Kim, Alexia N. Kim, Carter J. McCormick, Brian M. Stoltz
Summary: Interest in therapeutic discovery often leads to the preparation of natural product analogs, benefiting synthetic chemistry. Planning synthetic routes with late-stage diversification in mind can provide access to previously unavailable compounds, which is crucial for the synthesis of complex molecules.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Matyas Milen, Balint Nyulasi, Tamas Nagy, Gyula Simig, Balazs Volk
Summary: A novel synthesis approach for the late-stage tetracyclic key intermediate of lumateperone starting from commercially available quinoxaline is described. The tetracyclic skeleton was constructed efficiently using Fischer indole synthesis, with the advantage of inexpensive starting material and avoidance of borane-based reduction step, providing potential for scalability.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Igor Beckers, Galahad O'Rourke, Dirk De Vos
Summary: This study reports a regiospecific C-H arylation of a highly functionalized azepino[5,3,4-cd]indole scaffold lacking directing groups via Pd(II) and Cu(II) co-catalysis, which offers a promising method to surpass the limitations of traditional protecting groups or metal additives in late-stage C-H activation reactions. The direct C-H coupling was demonstrated in the convergent synthesis of the FDA approved anticancer drug rucaparib.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Luiz F. T. Novaes, Justin S. K. Ho, Kaining Mao, Kaida Liu, Mayank Tanwar, Matthew Neurock, Elisia Villemure, Jack A. Terrett, Song Lin
Summary: In this study, we developed a novel electrochemical method for the selective α-methylation of protected amines, which are structurally complex medicinal agents. This method demonstrates broad reaction scope, high functional group compatibility, and allows for late-stage functionalization of complex targets containing basic nitrogen groups. Additionally, this method can be combined with organozinc-mediated C-C bond formation, enabling the direct methylation of various amine derivatives and potentially accelerating drug discovery efforts.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Applied
Yan-Cheng Hu, Ying Li, Ding-Wei Ji, Heng Liu, Hao Zheng, Gong Zhang, Qing-An Chen
Summary: The study presents a straightforward method for C2 prenylation of NH indoles with good regioselectivity and broad substrate scope. The one-step process, catalyzed by acid, is efficient and atom-economical, suitable for late-stage diversification of tryptophan-based peptides and concise synthesis of tryprostatin B.
CHINESE JOURNAL OF CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Tamiris Reissa Cipriano da Silva, Rafaela Brito Oliveira, Arthur Luiz Miranda Nicastro, Rodrigo Portes Ureshino, Cristiano Raminelli
Summary: A dehydroaporphine intermediate obtained via benzyne chemistry was used to accomplish the enantioselective total synthesis of (S)-nuciferine, the first total synthesis of (& PLUSMN;)-urabaine, and our second-generation total synthesis of lysicamine. Low cytotoxicity and promising neuroprotective activity were observed for lysicamine and (& PLUSMN;)-urabaine.
Article
Chemistry, Organic
Riko Minami, Tsubasa Kasai, Keisuke Murata, Haruhiko Fuwa
Summary: In this study, a convergent total synthesis of (+)-muricatetrocin B, a tetrahydrofuran-containing acetogenin with potent and selective cytotoxicity against HT-29 human colon adenocarcinoma cell line, was achieved in 13 steps. The synthesis is highlighted by a late-stage sequential olefin cross-metathesis/Hartung-Mukaiyama cyclization for the assembly of the 2,5-trans-substituted tetrahydrofuran ring.
Article
Multidisciplinary Sciences
Peng Wang, Jiang Liu, Xiaomei Zhu, Zhengqing Kenry, Zhengqing Yan, Jiahui Yan, Jitong Jiang, Manlin Fu, Jingyan Ge, Qing Zhu, Yuguo Zheng
Summary: Cyclic peptides have attracted attention in the pharmaceutical industry, but there are limited methods for their synthesis. This study presents an efficient and direct method for peptide cyclization using rhodium(III)-catalyzed C(7)-H maleimidation. The resulting cyclic peptides exhibit higher bioactivity and can be used for creating peptide-drug conjugates.
NATURE COMMUNICATIONS
(2023)
