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
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
Multidisciplinary Sciences
David B. Konrad, Klaus-Peter Ruehmann, Hiroyasu Ando, Belinda E. Hetzler, Nina Strassner, Kendall N. Houk, Bryan S. Matsuura, Dirk Trauner
Summary: A stereoselective synthesis of TTX from a glucose derivative is presented, proceeding via 22 steps. This method provides ready access to biologically active derivatives.
Article
Chemistry, Applied
Xiang Shi, TianTian Xia, Brooke E. McKamey, Xian Wu, Yue Sun, Weifeng Zhou, Guangyan Zhang
Summary: In this study, an efficient synthesis of [6]-paradol was achieved in four steps with a 72.0% overall yield. The method utilized commercially available materials and allowed for convenient isolation with multiple crystallization without the need for column chromatography, resulting in a high-purity product of over 99.2% purity that is suitable for large-scale synthesis.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Multidisciplinary
Hong-Gang Cheng, Zhenjie Yang, Ruiming Chen, Liming Cao, Wen-Yan Tong, Qiang Wei, Qingqing Wang, Chenggui Wu, Shuanglin Qu, Qianghui Zhou
Summary: A concise total synthesis of (-)-berkelic acid is reported in eight linear steps, featuring a Catellani reaction/oxa-Michael cascade, a one-pot deprotection/spiroacetalization operation, and a late-stage Ni-catalyzed reductive coupling. Notably, four stereocenters are established from a single existing chiral center with excellent stereocontrol during the deprotection/spiroacetalization process, supported by DFT calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Lei Li, Weida Liang, Mario E. Rivera, Ye-Cheng Wang, Mingji Dai
Summary: A concise synthesis of (-)-GA18 methyl ester from commercially available and cheap andrographolide is reported. The synthesis involves intramolecular ene reaction, oxidative cleavage and aldol condensation, photochemical cycloaddition, and skeletal rearrangement.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Biochemistry & Molecular Biology
Zhiyuan Zhuang, Zhenbiao Luo, Sichen Yao, Yawen Wang, Yu Peng
Summary: A short synthesis of racemic Sacidumlignan B was achieved for the first time, involving a formal reductive coupling and a subsequent Friedel-Crafts cyclization to construct the dihydronaphthalene skeleton of this natural product.
Article
Chemistry, Organic
Yoshiyuki Manabe, Takuya Matsumoto, Yuka Ikinaga, Yuya Tsutsui, Shota Sasaya, Yuichiro Kadonaga, Akihito Konishi, Makoto Yasuda, Tomoya Uto, Changhao Dai, Kumpei Yano, Atsushi Shimoyama, Ayana Matsuda, Koichi Fukase
Summary: The study found that catalytic glycosylations using BF3·Et2O could efficiently proceed without the use of dehydrating agents, in contrast to traditional reactions requiring excess Lewis acid and additives. Mechanistic studies showed that chemical species formed by the reaction of in situ generated HF and glass vessels are involved in the catalytic cycle.
Article
Chemistry, Organic
Shivalal Banoth, Utkal Mani Choudhury, Kanakaraju Marumudi, Ajit C. Kunwar, Debendra K. Mohapatra
Summary: A concise and stereoselective synthesis of Curvulone B was achieved through utilizing tandem isomerization and C-O/C-C bond-forming reactions under Mukaiyama-type aldol conditions. Other key features of this synthesis include cross-metathesis, epimerization, and Friedel-Crafts acylation.
Article
Chemistry, Multidisciplinary
Masahito Yoshida, Yuhi Okoshi, Hideo Kigoshi
Summary: A concise total synthesis of metacridamides A and B was achieved through repetitive vinylogous Mukaiyama aldol reactions and ynamide-mediated macrolactonization. The spectral data of the synthetic products matched those of the natural compounds, leading to the reassessment of the absolute configuration of the C-9 position as S.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Akriti Srivastava, Lakshmanan Palanivel, Sundarababu Baskaran
Summary: An efficient domino approach for the synthesis of biologically important 2-aminoindole derivatives has been developed using CuBr2-mediated SET oxidative cyclization as a key step. This one-pot multicomponent strategy utilizes readily available starting materials and demonstrates generality and scope with a wide variety of substrates, producing functionalized 2-aminoindoles in good yields. The synthetic power of this strategy is further exemplified in the concise synthesis of biologically important alkaloids, Phaitanthrin E and Tryptanthrin.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Yuanzhi Li, Mengqian Zhu, Liang Xu
Summary: A concise biogenetically inspired formal synthesis of camptothecin has been developed, utilizing key reactions such as Pictet-Spengler reaction, intramolecular oxa-Diels-Alder reaction, and Winterfeldt biomimetic oxidation without the use of protecting groups.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Koji Morimoto, Kana Yanase, Tetsuya Kajimoto, Yasuyuki Kita
Summary: A method using hypervalent iodine reagents for oxidative glycosylation was discovered, resulting in the synthesis of sugars of different sizes, providing new possibilities for further research.
Article
Chemistry, Multidisciplinary
Naveen Diddi, Dale E. Ward
Summary: The total synthesis of dolabriferol C was achieved by a series of unique chemical reactions, simplifying the synthetic process significantly. This synthetic approach combines different stereochemical selectivities and enantioselective reactions, providing new insights for the study of related compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Ruiming Chen, Shihu Jia, Yuning Man, Hong-Gang Cheng, Qianghui Zhou
Summary: A concise total synthesis of (+/-)-stepharine and (+/-)-pronuciferine using readily available reagents as the starting materials is reported. This synthesis features a three-component Catellani reaction/Au-catalyzed 6-exo-dig cyclization for the assembly of 1-methylene-tetrahydroisoquinoline scaffold and an oxidative dearomatization for constructing spiro-cyclohexadienone scaffold.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Naoya Sagawa, Haruka Sato, Seijiro Hosokawae
Article
Chemistry, Organic
Naoya Sagawa, Hiroki Moriya, Seijiro Hosokawa
Article
Chemistry, Organic
Seijiro Hosokawa
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2017)
Review
Chemistry, Multidisciplinary
Seijiro Hosokawa
ACCOUNTS OF CHEMICAL RESEARCH
(2018)
Article
Chemistry, Organic
Kuniaki Tatsuta, Daisuke Sekine, Shinichi Hayama, Yasuhiro Kataoka, Shinya Hayashi, Seijiro Hosokawa
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Tatsuki Ohashi, Seijiro Hosokawa
Article
Chemistry, Organic
Sawato Murakoshi, Seijiro Hosokawa
Article
Chemistry, Organic
Aakash Sengupta, Seijiro Hosokawa
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Organic
Haruka Sato, Seijiro Hosokawa
Article
Chemistry, Organic
Aakash Sengupta, Seijiro Hosokawa
Article
Chemistry, Organic
Yoshiyasu Ichikawa, Toshiki Yamasaki, Keisuke Nakanishi, Yutaro Udagawa, Seijiro Hosokawa, Toshiya Masuda
SYNTHESIS-STUTTGART
(2019)
Article
Chemistry, Organic
Kanade Kirita, Seijiro Hosokawa
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Yuya Nakagawa, Keigo Yamaguchi, Seijiro Hosokawa
Summary: The [3 + 2]-cycloaddition reaction between N-tosylaziridines and alpha,beta-unsaturated ketones was promoted with lithium iodide, providing high yields of the target products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Seijiro Hosokawa
Summary: Different types of polyketide skeletons, including polyacetate-type and acetate-propionate hybrid-type, have been successfully synthesized through remote asymmetric induction reactions. Selective formation of anti- and syn-adducts was achieved by using different substrates, demonstrating good stereochemical control. The stereo-control systems in the reactions of different types were discussed, and the chiral auxiliary indirectly influenced the stereoselectivity in the reactions.
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2021)
Article
Chemistry, Organic
Seijiro Hosokawa, Keisuke Nakanishi, Yutaro Udagawa, Mitsutoshi Maeda, Seiya Sato, Keiji Nakano, Toshiya Masuda, Yoshiyasu Ichikawa
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)