Article
Chemistry, Organic
Zachary A. Tolchin, Dallas M. Dukes, Leanna M. Gharbaoui, Joel M. Smith
Summary: A synthesis of the natural product thebaine from commercially available starting materials is described, which involves dearomatization and coupling reactions of simple aromatic compounds. This method allows for the production of two unnatural opioid derivatives, with the goal of developing synthetic opioid analogs of Naloxone. Furthermore, a catalytic asymmetric dearomatization using anion-pairing catalysis is proposed for the enantioselective synthesis of all reported targets.
Article
Plant Sciences
Robin Huber, Laurence Marcourt, Alexey Koval, Sylvain Schnee, Davide Righi, Emilie Michellod, Vladimir L. Katanaev, Jean-Luc Wolfender, Katia Gindro, Emerson Ferreira Queiroz
Summary: A series of complex phenylpropanoid derivatives were obtained by chemoenzymatic biotransformation. These compounds showed anti-Wnt activity and have potential applications.
FRONTIERS IN PLANT SCIENCE
(2022)
Article
Chemistry, Organic
Minami Odagi, Taisei Matoba, Kazuo Nagasawa
Summary: In this paper, we describe the enantioselective total syntheses of cepharatines A-D, which are members of the hasubanan alkaloid family and feature an unusual tetracyclic skeleton including an azabicyclo[3.3.1]nonane motif. The key reaction involves a regio-divergent oxidative phenolic coupling reaction that efficiently affords the tricyclic core structure of hasubanan with different substitution patterns on the A-ring, including the all-carbon quaternary stereogenic center at C13, in a single step. Furthermore, the characteristic tetracyclic azabicyclo[3.3.1]nonane motif is constructed via a bioinspired cascade reaction involving the retro-aza-Michael reaction/hemiaminal formation.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Applied
Jie Zheng, Han Xu, Junqiang Fang, Xing Zhang
Summary: Human milk oligosaccharides (HMOs) are complex glycans that play a critical role in infant health. However, their limited availability hinders their use. This review examines the progress in enzymatic and chemoenzymatic synthesis of HMOs, and discusses the challenges and opportunities in large-scale synthesis of HMOs.
CARBOHYDRATE POLYMERS
(2022)
Article
Chemistry, Organic
Fei Cao, Weiwei Gao, Xiaodong Wang, Zhihan Zhang, Gaofeng Yin, Yuqing Wang, Zhao Li, Tao Shi, Yongsheng Hou, Jinhong Chen, Zhen Wang
Summary: The proposed structures of parvistemoamide have been achieved by macrolactamization, but characterization data of synthetic samples did not match with those of the natural sample. The transformation of the highly strained 10-membered lactam ring in parvistemoamide into the pyrrolo[1,2-alpha]-azepine nucleus in stemoamide is accomplished for the first time by either transannular cyclization or Pilli's transformation. This research may promote the total synthesis of other more complex stemoamide-type or medium-sized-ringcontaining Stemona alkaloids.
Article
Chemistry, Organic
Barbara Chatinovska, Rokas Gegevicius, Edvinas Orentas
Summary: This study obtains rapid access to both enantiomers of vellosimine and its derivatives from a readily affordable precursor. The strategy utilized desymmetrization via intramolecular cyclization to assemble a key intermediate with two differentiated carbonyl groups. The late-stage site selective indolization allows for a concise synthesis of vellosimines and a straightforward diversification of the alkaloid scaffold.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Huan He, Fanglin Xue, Zhao Hu, Peng Li, Qian Xiao, Maojie Zhang, Fei Xue, Dan Zhang, Hao Song, Xiao-Yu Liu, Zhibing Zheng, Song Li, Wu Zhong, Yong Qin
Summary: Morphine and its related alkaloids are commonly used natural medicines. However, the current industrial manufacturing process of these compounds causes environmental issues. In this study, researchers developed an efficient total synthesis method for opioids such as codeine, oxycodone, naloxone, and naltrexone. The key step in this synthesis is the Pd-catalyzed dearomatization arene coupling reaction using an inexpensive and stable phosphonium ligand.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Biochemistry & Molecular Biology
Rukman Muslimin, Natsumi Nishiura, Aiko Teshima, Kiep Minh Do, Takeshi Kodama, Hiroyuki Morita, Cody Wayne Lewis, Gordon Chan, Ahmed Taha Ayoub, Kenji Arakawa
Summary: In this study, the importance of the 8-lactone ring in lankacidin C was investigated. The results showed that the 8-lactone moiety has minimal impact on the antitumor activity of lankacidin-group antibiotics.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Plant Sciences
Kota Nishiuchi, Hirofumi Ohashi, Kazane Nishioka, Masako Yamasaki, Masateru Furuta, Takumi Mashiko, Shusuke Tomoshige, Kenji Ohgane, Shinji Kamisuki, Koichi Watashi, Kouji Kuramochi
Summary: A new synthetic method for this type of alkaloids was reported in this study, and some derivatives were found to exhibit antiviral activities against hepatitis C virus and severe acute respiratory syndrome coronavirus 2. The results highlight the importance of the exomethylene moiety on the diketopiperazine ring for the antiviral activities of these compounds.
JOURNAL OF NATURAL PRODUCTS
(2022)
Review
Chemistry, Organic
Hui-Jing Wang, Yang-Yang Zhong, You-Cai Xiao, Fen-Er Chen
Summary: This review summarizes the historical perspective and recent advances in the stereoselective synthesis of beta-nucleosides and their analogues, and introduces three synthetic strategies.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Medicinal
Pan-Pan Fu, Qun Wang, Qing Zhang, Yang Jin, Jin Liu, Kai-Xian Chen, Yue-Wei Guo, San-Hong Liu, Xu-Wen Li
Summary: The total synthesis and structure modification of the marine natural product naamidine J were achieved based on structure-relationship analyses. These compounds were tested for their ability to inhibit PD-L1 protein expression in human colorectal adenocarcinoma cells. Compound 11c efficiently suppressed PD-L1 expression in cells and exhibited antitumor effects in mice by reducing PD-L1 expression and enhancing T-cell immunity. This research may contribute to the discovery of new tumor immunological drug leads derived from marine natural products.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Saad Alrashdi, Federica Casolari, Aziz Alabed, Kwaku Kyeremeh, Hai Deng
Summary: This report presents a pilot study on the biotransformation of indole-containing acyloins. The study utilizes the enzymatic combination of PfTrpB variant, LAAO, and NzsH to produce acyloins with different indole substituents. The results show that NzsH has a broad substrate profile and can be further optimized via directed evolution.
Article
Biochemistry & Molecular Biology
Istvan Koteles, Karoly Mazak, Gergo Toth, Peter Horvath, Eszter Kiss, Boglarka Tuz, Sandor Hosztafi
Summary: Morphine derivatives with C-3 phenolic hydroxy group can be used for synthesizing 3-O-functionalized molecules, which are suitable for immunization and immunoassays. Using ethyl bromo- and chloroacetate as O-alkylating agents allows the production of 3-O-carboxyalkyl derivatives with free carboxylic groups for further modification and conjugation.
CHEMISTRY & BIODIVERSITY
(2021)
Article
Chemistry, Organic
Philipp Gross, Heiko Ihmels
Summary: A novel azoniahetarene, named benzo[b]-indolonaphthyridinium, was unexpectedly synthesized by a specific reaction condition. The products exhibited high fluorescence intensity in polar solvents and showed high affinity to DNA through intercalation. Additionally, DNA-binding sempervirine derivatives were also synthesized under the same conditions, indicating that the reaction pathway is determined by the substrate structure.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Rajendra S. Rohokale, Qingjiang Li, Zhongwu Guo
Summary: The synthetic strategy utilizing a single starting material and stepwise elongation of the glycan, as well as on-site remodeling of the lipid, successfully synthesized GSL compounds with different functionalities and sugar chains.
JOURNAL OF ORGANIC CHEMISTRY
(2021)