Article
Chemistry, Multidisciplinary
Wei Cao, Yingchao Dou, Cyrille Kouklovsky, Guillaume Vincent
Summary: The first total synthesis of the monoterpene indole alkaloids ophiorrhine A is reported via a late stage bioinspired intramolecular Diels-Alder cycloaddition. The synthesis includes the construction of the indolopyridone moiety, cyclodehydration, and the desired spontaneous intramolecular Diels-Alder cycloaddition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Tomoya Mashiko, Yuta Shingai, Jun Sakai, Shogo Kamo, Shinya Adachi, Akinobu Matsuzawa, Kazuyuki Sugita
Summary: In this study, the first total synthesis of cochlearol B, a meroterpenoid natural product with a unique pentacyclic structure, was described. Key steps including oxidative cyclization and subsequent intramolecular [2+2] photocycloaddition allowed efficient access to cochlearol B with a longest linear sequence of 16 steps and 9% overall yield. Single-crystal X-ray crystallographic analysis confirmed the stereochemistry of cochlearol B.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Jun-Li Li, Xiaoying Niu, Yi-Fan Song, Jian-Long Du, Shigang Shen, Xiu-Long Yang
Summary: A single cobaloxime-catalyzed acceptorless dehydrogenative cyclization method was developed for the synthesis of 1,3-dicarbonyl compounds with quinone and benzene rings. This method does not require bases or oxidants, offering a highly atom-economical strategy.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Meng-Yue Cao, Bin-Jie Ma, Qing-Xiu Gu, Bei Fu, Hai-Hua Lu
Summary: This paper reports a concise protecting-group-free total synthesis of Daphenylline, a structurally unique member of the triterpenoid Daphniphyllum natural alkaloids. Key reactions include an intramolecular oxidative dearomatization reaction, a tandem reductive amination/amidation double cyclization reaction, and a highly enantioselective rhodium-catalyzed hydrogenation reaction.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Shogo Kamo, Hitomi Kurosawa, Akinobu Matsuzawa, Kazuyuki Sugita
Summary: This study presented a successful eight-step enantioselective synthesis of (-)-lamellodysidine A, a sesquiterpene natural product with a unique tetracyclic skeleton, obtained from a marine sponge. The key to this synthesis is a cascade reaction involving an intramolecular Diels-Alder reaction, and the stereochemistry and absolute configuration were confirmed through single-crystal X-ray crystallography.
Article
Chemistry, Organic
Shogo Kamo, Hitomi Kurosawa, Akinobu Matsuzawa, Kazuyuki Sugita
Summary: In this study, an eight-step enantioselective synthesis of (-)-lamellodysidine A was achieved. The key to the synthesis is a cascade reaction that includes an intramolecular Diets-Alder reaction. Single-crystal X-ray crystallographic analysis of the synthetic (-)-lamellodysidine A confirmed the proposed stereochemistry and absolute configuration.
Article
Chemistry, Multidisciplinary
Yusuke Imamura, Kyohei Takaoka, Yuma Komori, Masanori Nagatomo, Masayuki Inoue
Summary: This study presents a 34-step synthesis of Taxol, involving inter- and intramolecular radical reactions to connect the A- and C-ring fragments and cyclize the B-ring. The A- and C-ring functional groups were then efficiently modified using newly developed selective reactions. The construction of the D-ring and its conjugation with the beta-amino acid led to the successful synthesis of Taxol. This synthesis provides useful insights for the design of multistep syntheses of diverse bioactive natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Tingting Cao, Lei Zhu, Jun Huang, Zhen Yang
Summary: This study successfully installed a sterically congested all-carbon quaternary center for the first time via a Pd-catalyzed cascade diarylation, providing a new method for the synthesis of complex organic compounds.
Article
Chemistry, Multidisciplinary
Wei Wei, Ka Key Cheung, Ran Lin, Lam Cheung Kong, Ka Lok Chan, Herman H. Y. Sung, Ian D. Williams, Rongbiao Tong, Zhenyang Lin, Guochen Jia
Summary: This paper describes a unique benzannulation strategy for the regioselective de novo synthesis of densely functionalized phenols. By utilizing a metal-mediated formal [2+2+1+1] cycloaddition reaction of two different alkynes and two molecules of CO, a series of densely functionalized phenols were obtained. This benzannulation strategy allows for efficient installation of up to five different substituents on a phenol ring, resulting in a substitution pattern distinct from those obtained from Dotz and Danheiser benzannulations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Pradip S. Waghmare, Sreenivasulu Chinnabattigalla, Satyanarayana Gedu
Summary: This paper reports a one-pot synthesis of functionalized naphthyl ketones via intermolecular Suzuki-Miyaura coupling and intramolecular aldol-type condensation. The method displays a broad substrate scope, good functional group tolerance, and enables the synthesis of aromatic-aliphatic hybrid frameworks with interesting structural features starting from readily available materials.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Thien Nhan Lu, Minjung Kwak, Mallesham Samala, Minji Son, Jungjoong Hwang, Suresh Mandava, Thuy Trang Pham, Haeil Park, Hyoungsu Kim, Deukjoon Kim, Jongkook Lee
Summary: A highly stereoselective asymmetric total synthesis of (-)-jimenezin (1), a potent anticancer acetogenin, was efficiently completed using a sequential intramolecular amide enolate alkylation (IAEA) technique. The presence of the oxygen atom in the adjacent tetrahydropyran ring was identified to be crucial for the complete stereoselectivity during the second IAEA step, resulting in the formation of a conformationally flexible tetrahydrofuran with perfect stereocontrol.
Article
Chemistry, Organic
Dong-Hyun Kim, Hyo-Mi Kim, Ji-Su Lim, Hyun-Woo Lee, Cheon-Gyu Cho
Summary: This article presents a new synthetic route for the asymmetric total synthesis of (+)-decursivine and (+)-serotobenine. The key breakthroughs include the construction of a crucial eight-membered 3,4-fused tricyclic indole ring and the stereocontrolled assembly of the dihydrobenzofuran subunit. The target natural compounds were obtained through selective epimerization and removal of amine masking groups.
Article
Chemistry, Multidisciplinary
Chun-Hong Yeh, Ya-Jou Chang, Tsung-Juin Lin, Cheng-Chung Wang
Summary: Infection with Campylobacter jejuni results in severe diarrhea, posing a significant threat to young children in underdeveloped countries. Due to the rise in antibiotic resistance, there is a need to develop a new therapy.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Chun-Hong Yeh, Ya-Jou Chang, Tsung-Juin Lin, Cheng-Chung Wang
Summary: This article presents a total synthesis of a C. jejuni NCTC11168 capsular polysaccharide repeating unit using an intramolecular anomeric protection (iMAP) strategy. The synthesis was completed in 28 steps, including the preparation of building blocks, construction of the tetrasaccharide skeleton, and functional group transformations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Tereza Edlova, Hana Dvorakova, Vaclav Eigner, Tomas Tobrman
Summary: Easily available disubstituted cyclobutenes were regioselectively halogenated at the allylic position by means of a reaction with bromine. The regioselectivity of bromination is controlled by the presence of a carbocation-stabilizing group. The prepared disubstituted 3-bromocyclobutenes were converted into the corresponding disubstituted cyclobutenones. The proposed mechanism behind the bromination reaction was based on the performed experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
