Article
Plant Sciences
Adrien Jagora, Jean-Francois Gallard, Mehdi A. Beniddir, Pierre Le Pogam
Summary: Lyaline, originally proposed as a harman-1,4-dihydropyridine derivative, was later found to be the first naturally occurring nacycline analogue after a total synthesis proved its instability. This structure revision substantiates a type of chemical reactivity reported in 1975 regarding strictosidine.
JOURNAL OF NATURAL PRODUCTS
(2021)
Review
Chemistry, Applied
Hong Yan, Fen-Er Chen
Summary: This review highlights the recent progress in solid-phase total synthesis of naturally occurring small peptides from 2014 to July 2021, which not only aids in the identification of peptide structures and synthesis of analogues, but also simplifies the isolation of intermediates.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Omer Bayazeid, Emirhan Nemutlu, Cemil Can Eylem, Mert Ilhan, Esra Kupeli-Akkol, Hande Karahan, Pelin Kelicen-Ugur, Tayfun Ersoz, Funda N. Yalcin
Summary: In this study, a conformer library of FDA-approved drugs was screened to identify similar drugs to roemerine, revealing five potential candidates. Metabolomics study showed that roemerine impacts the alanine-aspartate-glutamate pathway in cell lysate and cultured medium. Furthermore, roemerine was found to increase intracellular BDNF protein expression and intercellular 5-HT level, indicating its neuronal activity in SH-SY5Y cell line.
NATURAL PRODUCT RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Li-Xuan Li, Long Min, Tian-Bing Yao, Shu-Xiao Ji, Chuang Qiao, Pei-Lin Tian, Jianwei Sun, Chuang-Chuang Li
Summary: The first total synthesis of daphgraciline, a member of Daphniphyllum yuzurine-type alkaloids, has been achieved. The unique structure of the yuzurine-type subfamily was efficiently assembled using a novel method, and the complex skeleton and key moiety were successfully constructed. This study provides a foundation for the further synthesis of enantioenriched daphgraciline with high stereochemistry.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Peng-Zhen Sheng, Lu-Lu Li, Zhi-Bin Ni, Kun Wei, Yu-Rong Yang
Summary: Cephalotine A, a newly isolated alkaloid from Cephalotaxus, was successfully synthesized enantioselectively via three crucial reactions. These involved SmI2-mediated radical cyclization of lactone and aldehyde for the final ring formation, Chang's iridium-catalyzed C-H amidation for constructing pyrrolidone stereoselectively, and Carreria's dual Ir/amine catalyzed allylation to introduce the neighboring tertiary stereocenters.
Article
Chemistry, Organic
Jianquan Zhu, Chao Zhang, Luyi Liu, Chaoyun Xue, Yukun Cai, Xiao-Yu Liu, Fei Xue, Yong Qin
Summary: This paper presents an asymmetric total synthesis of the sarpagine alkaloid (-)-normacusine B. The key features of this synthesis include a photocatalytic nitrogen-centered radical cascade reaction, a titanium-mediated intramolecular amide-alkene coupling, and a nickel-catalyzed reductive Heck coupling.
Article
Chemistry, Organic
Hongbin Zhai, Zhenhua Wang, Kewei Chen, Tian-Yu Sun, Jian Wei, Yun-Dong Wu
Summary: The first asymmetric total synthesis of indole alkaloid arbophyllidine has been achieved, featuring key reactions such as intramolecular reductive Heck reaction, Fischer indolization, and oxidative lactonization. Density functional theory calculations were employed to provide a comprehensive understanding of the oxidative lactonization.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Si-Hua Hou, Adriana Y. Prichina, Guangbin Dong
Summary: The development of a deconstructive strategy for the first asymmetric synthesis of (-)-thebainone A was described, utilizing an enantioselective C-C bond activation and a C-O bond cleavage reaction. The newly optimized conditions show broad substrate scope and excellent enantioselectivity (up to 99.5:0.5 er). The synthesis of (-)-thebainone A was completed by taking advantage of boron-mediated ether bond cleavage through two complementary routes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Plant Sciences
Ting -Yu Lin, Chieh-Yu Chou, Yu-Hsuan Chen, Chien-Kuo Ku, Ming-Jaw Don
Summary: A total synthesis of four flavans with a furan ring in different positions was achieved successfully through reduction and deoxygenation steps from flavanone. Compound 2 was identified as the naturally occurring moracinflavan E based on NMR spectral data comparison.
PHYTOCHEMISTRY LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Varun Pratap Singh, Anup Singh Pathania, Sonia Sharma, Fayaz Ahmed Malik, Anil Kumar, Deepika Singh, Ram A. Vishwakarma
Summary: The lipopeptaibol D exhibited potent cytotoxic activity and the C-terminal aldehyde analogue resulting from its lead optimization showed nearly twofold enhanced cytotoxicity against MDA-MB-231 breast cancer cell lines.
Article
Chemistry, Organic
Pramchai Deelertpaiboon, Sopanat Kongsriprapan, Suppachai Krajangsri, Nolan M. Betterley, Chutima Kuhakarn, Vichai Reutrakul
Summary: The asymmetric synthesis of the novel pyranonaphthoquinones ventilanone A and ventilanone B, isolated from the Thai endemic plant Ventilago harmandiana, is achieved using L-rhamnose and gallic acid as starting materials. Key reactions involve the use of a newly introduced reagent, PhSCF2H/SnCl4, for formylation of sterically hindered aromatics with electron-withdrawing methyl esters, and the efficient Hauser annulation of phenylthiophthalides with optically active glycals derived from L-rhamnose. These synthetic methodologies solve the long-standing problem of formylation of sterically hindered aromatics with electron-withdrawing groups and can be applied to the synthesis of analogues with substituents on the aromatic and pyran rings.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Bing-Chao Yan, Min Zhou, Jian Li, Xiao-Nian Li, Shi-Jun He, Jian-Ping Zuo, Han-Dong Sun, Ang Li, Pema-Tenzin Puno
Summary: Isoscopariusin A, isolated from Isodon scoparius, was identified as an unsymmetrical meroditerpenoid with a sterically congested carbon skeleton. Gram-scale synthesis was achieved in 12 steps, with selective inhibition of T-cell proliferation as a significant biological activity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Liu-Yang Pu, Fan Yang, Ji-Qiang Chen, Ying Xiong, Jian-Hua Xie, Qi-Lin Zhou
Summary: The enantioselective total synthesis of the pentacyclic proaporphine alkaloid (-)-misramine was achieved, featuring key reactions including Pictet-Spengler cyclization and Baeyer-Villiger oxidation. The absolute configuration of the pentacyclic framework was determined through X-ray single-crystal analyses.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Multidisciplinary Sciences
Yingfu Lin, Rui Zhang, Di Wang, Tim Cernak
Summary: Efficient chemical synthesis is crucial for meeting the future demands of pharmaceuticals, materials, and agrochemicals. While the automation of retrosynthetic analysis for moderately complex molecules has been ongoing for decades, the vast number of possible routes has posed challenges for computer hardware and software until recently. In this study, we introduce a computational strategy that combines computer-aided synthesis planning with molecular graph editing to minimize the synthetic steps needed for producing alkaloids. Through the utilization of high-impact key steps identified in computer-generated retrosynthesis plans using graph edit distances, we have successfully achieved an enantioselective three-step synthesis of (-)-stemoamide.
Article
Plant Sciences
Sangil Kwon, Sanha Lee, Joonseong Hur, Keebeom Ko, Xiang Fei, Kwang Won Jeong, Kamakshi Sishtla, Anbukkarasi Muniyandi, Munhyung Bae, Timothy W. Corson, Seung-Yong Seo
Summary: Dracaeconolide B, a natural homoisoflavane, was isolated from the red resin of Dracaena cochinchinensis. The structure of dracaeconolide B was revised through synthesis of similar compounds and analysis using NMR spectroscopy. The antiangiogenic activity of dracaeconolide B and related compounds was examined, providing potential insights for drug discovery in neovascular eye diseases.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Chemistry, Medicinal
Shiori Oshimi, Yuichiro Tomizawa, Yusuke Hirasawa, Toshio Honda, Wiwied Ekasari, Aty Widyawaruyanti, Marcellino Rudyanto, Gunawan Indrayanto, Noor Cholies Zaini, Hiroshi Morita
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2008)
Article
Chemistry, Organic
Marcellino Rudyanto, Koichi Kobayashi, Toshio Honda
Article
Pharmacology & Pharmacy
Alvan F. Shalas, Siswandono, Marcellino Rudyanto
JOURNAL OF YOUNG PHARMACISTS
(2018)
Article
Chemistry, Organic
M Rudyanto, M Toyota, N Kagawa, M Ihara
Article
Chemistry, Organic
M Toyota, M Rudyanto, M Ihara
JOURNAL OF ORGANIC CHEMISTRY
(2002)
Article
Chemistry, Organic
M Toyota, M Rudyanto, M Ihara
TETRAHEDRON LETTERS
(2000)