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)
Article
Chemistry, Organic
Bolin Chen, Yufen Yang, Xijing Zhang, Dongdong Xu, Yuanjun Sun, Yue Chen, Liang Wang
Summary: In this study, concise and divergent total syntheses of fusicoccane members brassicicenes A, R, and T were reported. The key feature of the synthesis is the rapid construction of the 5/8/5 tricyclic core via four steps, followed by concise oxidation state adjustment.
Article
Chemistry, Organic
Shuyang Li, Jack A. O'Hanlon, Andrew Mattimoe, Helena D. Pickford, Lucy A. Harwood, Luet L. Wong, Jeremy Robertson
Summary: Two total syntheses for trigoxyphins K and L, tricyclic terpenoids from Trigonostemon xyphophylloides, are presented. The first synthesis involves electrophlic cyclization and hydroxybutenolide formation to produce trigoxyphin L, followed by Luche reduction to obtain trigoxyphin K. The second synthesis employs tetralone ring expansion and lactonization-isomerization to yield trigoxyphin K, which is then converted to trigoxyphin L through enolate oxygenation.
Article
Chemistry, Organic
Hesi Yang, Yan Zhang, Wei Chen, Hongliang Shi, Liang Huo, Jia Li, Huilin Li, Xingang Xie, Xuegong She
Summary: This article describes the first total syntheses of two novel ansamacrolactams, (+/-)-catellatolactams A and B, in 5 and 8 steps, respectively. The synthesis strategy involves an amidation reaction, a regioselective C-H insertion, and an RCM reaction to form the macrocycles with E-olefin. The concise and scalable synthesis provided over 200 mg of the target molecules.
Article
Pharmacology & Pharmacy
Ikumi Washio, Takeo Nakanishi, Naoki Ishiguro, Bojan Bister, Ikumi Tamai
BIOPHARMACEUTICS & DRUG DISPOSITION
(2019)
Article
Pharmacology & Pharmacy
Hiroshi Arakawa, Natsumi Amezawa, Tomomichi Katsuyama, Takeo Nakanishi, Ikumi Tamar
DRUG METABOLISM AND PHARMACOKINETICS
(2019)
Article
Multidisciplinary Sciences
Khine Myint, Riya Biswas, Yan Li, Nancy Jong, Stephen Jamieson, Johnson Liu, Catherine Han, Christopher Squire, Fabrice Merien, Jun Lu, Takeo Nakanishi, Ikumi Tamai, Mark McKeage
SCIENTIFIC REPORTS
(2019)
Article
Chemistry, Organic
Kakeru Maeda, Ryo Murakami, Fuyuhiko Inagaki
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Organic
Ryo Murakami, Fuyuhiko Inagaki
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Multidisciplinary
Nozomi Arakawa, Kazunori Nagao, Ryo Murakami, Yuto Sumida, Hiroshi Arakawa, Fuyuhiko Inagaki, Hirohisa Ohmiya
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2020)
Article
Medicine, Research & Experimental
Masamichi Hirayama, Yusuke Hoshino, Kazuyoshi Yoshii, Ryoko Toda, Yoshihiro Kawabata, Takeo Nakanishi, Ikumi Tamai
MOLECULAR PHARMACEUTICS
(2020)
Article
Chemistry, Medicinal
Misaki Nakano, Rikako Nakamura, Yuto Sumida, Kazunori Nagao, Taniyuki Furuyama, Fuyuhiko Inagaki, Hirohisa Ohmiya
Summary: The optical properties of fluorescent unit-conjugated aliphatic oxaboroles have been studied, showing good fluorescence quantum yields and selective recognition of D-ribose and D-ribose containing molecules. Molecular recognition led to significant fluorescence quenching, suggesting the potential for a boron-based NAD sensor probe.
CHEMICAL & PHARMACEUTICAL BULLETIN
(2021)
Article
Chemistry, Medicinal
Ryo Murakami, Kakeru Maeda, Fuyuhiko Inagaki
Summary: The synthesis of 2,2-dimethyloxepane frameworks via the 7-endo-trig cyclization of ene-diol using metal catalysts or Brønsted acid has been developed. Metal catalysts selectively react between 1,1,3-trisubstituted alkenes and alcohols, while Brønsted acid reacts with a variety of alkene types providing different cyclic ethers.
CHEMICAL & PHARMACEUTICAL BULLETIN
(2021)
Article
Chemistry, Organic
Ryo Murakami, Hiroto Tanishima, Daisuke Naito, Hikari Kawamitsu, Ryoya Kamo, Ayaka Uchida, Kazuki Kawasaki, Chihiro Kiyohara, Motoki Matsuo, Kakeru Maeda, Fuyuhiko Inagaki
Summary: The study synthesized a cationic catalyst Au(DPB)X-3 with a specific ligand, which was successfully utilized in a specific reaction of yne-indoles.
TETRAHEDRON LETTERS
(2021)
Article
Pharmacology & Pharmacy
Masato Kobayashi, Asuka Mizutani, Yuka Muranaka, Kodai Nishi, Hisakazu Komori, Ryuichi Nishii, Naoto Shikano, Takeo Nakanishi, Ikumi Tamai, Keiichi Kawai
Summary: This study used whole-body imaging with [I-123]MIBG to investigate the absorption of cationic anticancer drugs and medicines in the gastrointestinal tract. The results showed different uptake mechanisms mediated by OCTN and OCT, which were affected by inhibitors L-carnitine and cimetidine. Furthermore, the accumulation of [I-123]MIBG was significantly altered in DSS-induced experimental colitis mice and mice with cimetidine loading. Therefore, [I-123]MIBG imaging can be used to estimate gastrointestinal absorption via OCTN and/or OCT in the small intestine.
Article
Chemistry, Organic
Hiroto Tanishima, Ryo Murakami, Fuyuhiko Inagaki
Summary: A novel cationic copper catalyst was synthesized and found to enhance the Mukaiyama-Aldol reaction, leading to the formation of protected tertiary alcohols.
TETRAHEDRON LETTERS
(2022)
Article
Pharmacology & Pharmacy
Kakeru Sato, Asuka Mizutani, Yuka Muranaka, Jianwei Yao, Masato Kobayashi, Kana Yamazaki, Ryuichi Nishii, Kodai Nishi, Takeo Nakanishi, Ikumi Tamai, Keiichi Kawai
Summary: This study evaluated the distribution of radioiodine-125 labeled acetaminophen (I-125-AP) in the body after oral administration, aiming to estimate the absorption of anionic drugs in the gastrointestinal tract. The results showed that the uptake of I-125-AP was significantly higher in cells expressing certain transporters and inhibited by specific inhibitors. Furthermore, the distribution of I-125-AP in mice indicated that the small intestine plays a crucial role in the absorption process mediated by OATPs, OATs, and/or MRPs.
Review
Chemistry, Organic
Ryo Murakami, Fuyuhiko Inagaki
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2020)
Article
Biology
Yoshinobu Nakamura, Takatoshi Sakaguchi, Ikumi Tamai, Takeo Nakanishi
