Article
Chemistry, Multidisciplinary
Pei Qu, Scott A. Snyder
Summary: The newly added annotinolides in the Lycopodium family have complex structures, and we have successfully achieved the total synthesis of three members using key operations such as gold(I)-catalyzed Conia-ene reaction and other challenging transformations. Furthermore, efforts to adjust the oxidation states and rearrange ring systems of the natural products shed light on their potential biogenesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Analytical
Omer Fantoukh, Yan-Hong Wang, Abidah Parveen, Mohammed E. Hawwal, Zulfigar Ali, Gadah A. Al-Hamoud, Amar G. Chittiboyina, Elizabeth Joubert, Alvaro Viljoen, Ikhlas A. Khan
Summary: Rooibos tea, traditionally consumed by indigenous South Africans, has antioxidant properties and various health benefits. A new method using liquid chromatography was developed to analyze the phenolic constituents in rooibos tea, providing a cost-effective way for quality control.
Article
Chemistry, Multidisciplinary
Baiyang Jiang, Mingji Dai
Summary: We report the total syntheses of four hamigeran natural products with a 6-7-5 tricyclic carbon skeleton. A palladium-catalyzed intramolecular cyclopropanol ring-opening cross-coupling was used to build the central seven-membered ring, and a series of oxidations, including a challenging aromatic C-H oxidation, were employed to introduce the peripheral functionalities. This approach allowed us to achieve the first total syntheses of hamigeran C (14 steps), debromohamigeran I (12 steps), hamigeran I (13 steps), and hamigeran G (13 steps), significantly shorter than the previously reported longest linear sequence (24 steps).
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Kosuke Okada, Ken-ichi Ojima, Hirofumi Ueda, Hidetoshi Tokuyama
Summary: The synthesis of (+)-pleiocarpamine, (+)-voacalgine A and (+)-bipleiophylline was achieved in this study. The 10-step synthesis of (+)-pleiocarpamine features the construction of stereochemistry at the C16 position by radical cyclization and the synthesis of the highly strained cage-like structure via Pd-catalyzed intramolecular aromatic C-H functionalization. By modifying the biomimetic aerobic oxidative coupling of tryptophane derivatives catalyzed by FePc(CO2H)(8), the oxidative coupling of (+)-pleiocarpamine with pyrocatechuic acid produced (+)-voacalgine A. The total synthesis of (+)-bipleiophylline was completed by the second coupling of (+)-voacalgine A with (+)-pleiocarpamine or the one-pot couplings of 2 equiv of (+)-pleiocarpamine with pyrocatechuic acid.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Wenzhang Chen, Tingxiao Xu, Gaofeng Zhu, Bing Guo, Lei Tang, Jianta Wang
Summary: The convenient and facile syntheses of amorfrutin A and amorfrutin B have been successfully achieved in five steps starting from commercially available 2,4-dimethoxybenzoic acid, with overall yields of 32% and 22%, respectively. Key steps involved Ru(II)-catalyzed olefination and straightforward C-alkylation.
Article
Chemistry, Multidisciplinary
Gustav J. Wormer, Nikolaj L. Villadsen, Peter Norby, Thomas B. Poulsen
Summary: The highly concise asymmetric synthesis of Streptazone A and abikoviromycin was reported in this study, which involved a series of catalytic reactions. Unexpected transformations of streptazone A towards a cysteine mimic, N-acetylcysteamine, were discovered, including the formation of bis-thiol conjugation. The research provides a flexible access to these compounds for further studies on their direct biological targets.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jinjae Park, Cheol-Hong Cheon
Summary: Two routes for the synthesis of rucaparib have been developed, using commercially available starting materials and the cyanide-catalyzed imino-Stetter reaction as the key step. The second-generation synthesis achieved a higher overall yield and resolved issues from the first-generation synthesis.
Article
Chemistry, Organic
Tingting Zhou, Anquan Zheng, Wenge Zhang, Xiuxiang Lu, Huiyu Chen, Haibo Tan
Summary: A two-step protecting-group-free protocol enabled the synthesis of 3'-hydroxy-5,7-dimethoxy-4-O-2'-cycloflavan (1) and concise total synthesis of 4'-hydroxy-5,7-dimethoxy-4-O-2'-cycloflavan (8) through a PTSA triggered bioinspired cascade reaction. The successful synthesis of cycloflavan 8 and revision of the structure of a previously isolated flavonoid were achieved.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Atsushi Nakayama, Tenta Nakamura, Toshihiro Zaima, Saho Fujimoto, Sangita Karanjit, Kosuke Namba
Summary: The concise total synthesis of tronocarpine, a chippiine-type indole alkaloid, was achieved through a one-pot construction of a pentacyclic skeleton. This strategy, controlled by the stereocenter at the C14 position, can be used to synthesize other chippiine-type alkaloids with azabicyclo[3.3.1]nonane skeletons.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Hai-Hua Lu, Kang-Ji Gan, Fu-Qiang Ni, Zhihan Zhang, Yao Zhu
Summary: The concise total synthesis of salimabromide was achieved using a series of novel reactions, which allowed for the construction of its unique carbon skeleton and stereocenters.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Arindam Khatua, Pranay Shyamal, Souvik Pal, Ayan Mondal, Alakesh Bisai
Summary: A new synthesis method has been developed for the preparation of enantioenriched compounds with all-carbon quaternary stereogenic centers. The method has been successfully applied in the total synthesis of several important alkaloids.
CHEMICAL COMMUNICATIONS
(2022)
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
Chemistry, Multidisciplinary
Gleb A. Chesnokov, Karl Gademann
Summary: The marine-derived compound Peyssonnoside A was successfully synthesized for the first time in a concise, efficient, scalable, and highly diastereoselective manner. The aglucone peyssonnosol was achieved in 21% overall yield after 15 steps, with key reactions including Simmons-Smith cyclopropanation and Mukaiyama hydration controlled by the spatial structure of the substrates.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Fuhao Zhang, Jingwen Zeng, Mohan Gao, Linzhou Wang, Gen-Qiang Chen, Yixin Lu, Xumu Zhang
Summary: A practical synthetic strategy for enantioselective and divergent synthesis of prostaglandins was reported, involving the construction of multiply substituted five-membered rings through key enyne cycloisomerization and installation of crucial chiral centers using asymmetric hydrogenation. Common intermediates allowed for the production of various prostaglandins and related drugs in two steps, with the preparation of fluprostenol on a 20-gram scale.
Article
Multidisciplinary Sciences
Eleanor M. Landwehr, Meghan A. Baker, Takuya Oguma, Hannah E. Burdge, Takahiro Kawajiri, Ryan A. Shenvi
Summary: Neuroactive metabolites from the bark of Galbulimima belgraveana exhibit varying distributions among trees and are challenging to access through chemical synthesis due to intricate bond networks and dense stereochemistry. However, a new synthetic approach has been developed to reduce the synthetic burden and increase efficiency, allowing for further chemical exploration and biological investigation in Galbulimima alkaloid space.
