Article
Chemistry, Physical
Jing Yang, Sheng-Chao Huang, Yi Wang, Meng-Yuan Ji, Yan-Jun Hu
Summary: The research demonstrated that both CPT and HCPT form complexes with bovine serum albumin (BSA) through hydrogen bonding and electrostatic interactions. Furthermore, both CPT and HCPT bind to site I on BSA, altering the conformation of BSA.
JOURNAL OF MOLECULAR LIQUIDS
(2021)
Review
Nanoscience & Nanotechnology
Yukun Chen, Zhenzhi Wang, Xiaofan Wang, Mingliang Su, Fan Xu, Lian Yang, Lijun Jia, Zhanxia Zhang
Summary: Nano drug delivery systems have been developed to improve the stability and water solubility of HCPT, thus enhancing its anticancer effect. Current research on HCPT nanomedicines has made progress, but there are still limitations.
INTERNATIONAL JOURNAL OF NANOMEDICINE
(2022)
Article
Chemistry, Multidisciplinary
Jeremy Duczynski, Colin L. Raston, Keith A. Stubbs
Summary: Iminosugars are important compounds in the field of carbohydrate-based therapeutics, and a simple synthetic methodology utilizing the vortex fluidic thin film microfluidic reactor is effective in the synthesis of such compounds for diverse reaction types.
Article
Chemistry, Organic
Haruka Fujino, Masanori Nagatomo, Masayuki Inoue
Summary: Hikizimycin is a potent anthelmintic and antibacterial natural product with a complex structure that has attracted synthetic chemists since its structural determination in the early 1970s. Efforts have culminated in synthetic approaches including the synthesis of protected hikosamines and total synthesis of Hikizimycin, showcasing the evolution of modern natural product synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Roberto Serrano, Yaroslav D. Boyko, Lucas W. Hernandez, Aleksandras Lotuzas, David Sarlah
Summary: The concise total syntheses of oxidized norcembranoid terpenoids (-)-scabrolide A and (-)-yonarolide have been achieved in 10 and 11 steps, respectively, by integrating two chiral-pool-derived fragments, including a [5,5]-bicyclic lactone accessed through a powerful Ni-catalyzed pentannulation of functionalized cyclopentenone with methylenecyclopropane and subsequent fragmentation. Additional features included a Liebeskind-Srogl coupling, induction of a cyclization/elimination cascade by a zinc-amido base, and installation of a sensitive enedione motif by latestage ?-oxidation.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Raphael J. Zachmann, Kenzo Yahata, Mira Holzheimer, Maxime Jarret, Cornelia Wirtz, Alois Fuerstner
Summary: The structure of prorocentin has been revised through a flexible synthesis approach, showing that the previously proposed structure is incorrect. The new, more plausible structure was obtained using methods such as gold-catalyzed spirocyclization reactions. This study has important implications for the understanding of prorocentin's structure.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Joseph P. Tuccinardi, John L. Wood
Summary: This article describes the first total syntheses of the nor-furanocembranoid natural products (+)-ineleganolide and (-)-sinulochmodin C. The synthetic strategy is based on a transannular Michael reaction and a diastereoselective radical cyclization, and discusses the unexpected stereochemical nuances during the evolution and completion of the total synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Xinpei Cai, Lei Li, Ye-Cheng Wang, Jianhan Zhou, Mingji Dai
Summary: In this paper, we describe the complete synthesis of phleghenrines A and C from commercially available starting materials in 7 and 8 steps, respectively. Key steps include an inverse electron-demand Diels-Alder reaction between a masked o-benzoquinone and a N-protected enamine to generate a bicyclo[2.2.2]octenone core, a Bu''chner-Curtius-Schlotterbeck one-carbon insertion to expand the bicyclo[2.2.2]octenone to a bicyclo[3.2.2]nonenone, and Trauner's modified 2-pyridone synthesis to install the 2-pyridone moiety.
Article
Chemistry, Organic
Yingjie Wang, Biao Yu
Summary: The total syntheses of two antiangiogenic anthraquinone glycosides, aturanosides A and B, were achieved in an expeditious manner, emphasizing anthraquinone synthesis, phenol glycosylation, alpha-D-glucosaminoside installation, and judicious use of protecting groups.
Article
Chemistry, Organic
Nariyoshi Umekubo, Satoshi Yokoshima
Summary: In this study, the total syntheses of tropolone-containing natural products malettinins C and E were achieved. A nitro compound and a chiral enone were prepared through palladium-mediated nitromethylation and an organocatalyst-mediated asymmetric aldol reaction, respectively, and connected via a Michael reaction. The oxidative dearomatization of a phenol with a cyclic acetal moiety resulted in a spirocyclic dienone, which could be converted into a tropolone through a base-mediated ring-expansion reaction with elimination of the nitro group, providing a pathway to malettinins C and E.
Article
Chemistry, Organic
Joshua M. Nicholson, Glenn C. Micalizio
Summary: Asymmetric de novo syntheses of euphol and tirucallol have been achieved using a concise sequence of chemical steps featuring several modern stereoselective transformations. The preparative solution for these complex natural product synthesis problems departs significantly from biomimetic polyene cyclization chemistry. The syntheses involve various stereoselective reactions to establish tetracyclic structures with stereodefined quaternary centers, providing access to enantiodefined euphane and tirucallane systems.
Article
Chemistry, Multidisciplinary
Wenqiang Zhou, Tao Zhou, Mengxing Tian, Yan Jiang, Jiaojiao Yang, Shuai Lei, Qi Wang, Chongzhou Zhang, Hanyue Qiu, Ling He, Zhen Wang, Jun Deng, Min Zhang
Summary: Through the development of a new method and key reactions, the concise, collective, and asymmetric total syntheses of four schizozygane alkaloids, including the first asymmetric synthesis, have been achieved in only 11-12 steps from tryptamines.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Ming Wang, Ya Wu, Mei Xu, Sheng Liu
Summary: An efficient synthetic route to iheyamine A and its analogues was discovered, involving a crucial one-pot transformation that included C-C migration to form the characteristic seven-membered ring. Subsequent addition of acetone to iheyamine A initiated a cascade process to complete the total synthesis of iheyamine B.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ming Wang, Ya Wu, Mei Xu, Sheng Liu
Summary: An efficient synthetic route to iheyamine A and its analogues was discovered, involving a crucial one-pot transformation with C-C migration to form the characteristic seven-membered ring. The subsequent addition of acetone to iheyamine A initiated a cascade process leading to the complete total synthesis of iheyamine B.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hongchang Tian, Yinxia Wu, Xiujuan Li, Zhen Hao, Wenyan He, Xiangdi Huang, Wen Chen, Hongbin Zhang
Summary: In this article, we present the first total synthesis of Kopsaporine related alkaloids. Our structure-unit-based strategy utilizes intramolecular Pummerer rearrangement induced nucleophilic cyclization/aza-Prins cyclization to construct the hexahydrocarbazole skeleton, olefin migration vinylogous alkylation to establish the C20 all-carbon quaternary center, iridium complex mediated radical addition to fuse the aspidofractine framework, unprecedented IBX oxidation to introduce the alpha-hydroxyketone moiety, and bioinspired retro-Aldol/Aldol reaction to convert kopsaporine to kopsiloscine A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
