Article
Chemistry, Organic
Tushar M. Khopade, Kalyani Ajayan, Dona Mariya Vincent, Amy L. Lane, Rajesh Viswanathan
Summary: The research team successfully synthesized a derivative of the natural product nocardioazine B using a biomimetic approach, achieving high yield. This derivative exhibits potential as a treatment for multidrug-resistant cancer cells, offering a new strategy against resistant carcinomas. Additionally, this synthesis method provides direct access to related natural products.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xudong Wang, Ganlin Huang, Yun Wang, Jinghan Gui
Summary: Phomarol is an unusual 1(10-* 19)abeo-steroid molecule with a cycloheptene-1,3-diol motif, an aromatic B ring, and a functionalized tetrahydropyran ring. The synthesis of this natural product from sitolactone involves a 13-step convergent fragment coupling approach, including key transformations such as allylboration, decarboxylative elimination, C-H hydroxylation, biomimetic cyclization, and electrocyclization. Mechanistic studies reveal that the formation of the tetrahydropyran ring occurs through a silyl migration/intramolecular cyclization cascade instead of an epoxide-opening process.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Ziyue Xiong
Summary: Researchers have developed a sustainable synthetic method which has been successfully applied to the total synthesis of (-)-galanthamine.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Lilla Koser, Vivian Miles Lechner, Thorsten Bach
Summary: The first chemical total synthesis of the highly oxygenated polyketide enterocin has been achieved using a late-stage biomimetic reaction cascade. The synthesis involved assembling a pivotal precursor from three readily available building blocks, with a chiral dithioacetal representing the core fragment. Additional building blocks were attached to both ends of the core fragment through aldol reactions, leading to the installation of four stereogenic centers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Yinxin Liu, Jun Liu, Chuanfang Zhao, Yuguo Du
Summary: The stereoselective total synthesis of siladenoserinols A and D was achieved using carbohydrates as a chiral template. The key feature of this work is the construction of the medicinally privileged 6,8-DOBCO scaffold through a cascade reaction, which could facilitate bioactivity investigation of siladenoserinols.
Article
Chemistry, Multidisciplinary
Jiaxin Xie, Zhong Zheng, Xin Liu, Nan Zhang, Shinyoung Choi, Chuan He, Guangbin Dong
Summary: This study reports on the synthesis of phainanoids, a new class of dammarane-type triterpenoids with potent immunosuppressive activities and unique structural features. Efficient approaches have been established for the synthesis of key structural components. The asymmetric synthesis of (+)-phainanoid A has been achieved and novel estrone-derived analogues have also been prepared. The compounds show specific inhibition of lymphocyte proliferation, providing preliminary structure-activity relationship information.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Biochemistry & Molecular Biology
Wenxi Wu, Yu Mu, Bo Liu, Zixuan Wang, Peipei Guan, Li Han, Mingguo Jiang, Xueshi Huang
Summary: In this study, violacin A and twenty-five analogues were synthesized, showing that introduction of aliphatic amine moieties significantly improved the anti-inflammatory effect of violacin A, and aromatic ether substitution instead of ketone group at side chain was favorable to increase the activity. Analogues 7a and 16d were identified as the most effective anti-inflammatory candidates, acquiring anti-inflammatory ability through the inhibition of NF-KB signaling pathway.
BIOORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Mervic D. Kagho, Helen Hintersatz, Andreas Ihle, Haoxuan Zeng, Hedda Schrey, Wera Colisi, Philipp Klahn, Marc Stadler, Clemens Bruhn, Tobias Rueffer, Heinrich Lang, Klaus Banert
Summary: The racemic total synthesis of nitrabirine and its epimer 2-epi nitrabirine was achieved via a six-step route involving biomimetic late-stage heterocyclization. Biological evaluation revealed biofilm dispersal effects against Candida albicans for both compounds, along with moderate antibacterial activities and potent cytotoxic activities for specific derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Noah J. Sims, Weston C. Bonnet, Danielle M. Lawson, John L. Wood
Summary: Herein, the first total synthesis of (+)-alterbrassicicene C (2) is reported. Key features of this synthesis include an oxiranium mediated ether ring expansion, an oxa-Michael/retro-oxa-Michael cascade, and the installation of a vinyl methoxy ether moiety via Stille coupling.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Noah J. Sims, Weston C. Bonnet, Danielle M. Lawson, John L. Wood
Summary: This article describes the first total synthesis of (+)-alterbrassicicene C (2). Key features of the synthesis include an oxiranium-mediated ether ring expansion, an oxa-Michael/retro-oxa-Michael cascade, and installation of a vinyl methoxy ether moiety via Stille coupling.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Yifan Deng, Chia-Ping H. Yang, Amos B. Smith
Summary: The enantioselective total syntheses of (+)-peniciketals A and B have been achieved, with key synthetic transformations including ARC and Negishi cross-coupling, among others.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Bing-Bing Huang, Yi-Lu Zhao, Kaiyu Lei, Lin-Rui Zhong, Xiaoliang Yang, Zhu-Jun Yao
Summary: An 11-step enantioselective total synthesis of (+)-sieboldine A (1) has been achieved, in which intramolecular ketone/ester reductive coupling and TsOH-catalyzed displacement were successfully applied as key methodologies. Additionally, several full-skeleton analogues of 1 were synthesized, and their inhibitory effects on electric eel acetylcholinesterase were examined.
Article
Chemistry, Multidisciplinary
Xin Shu, Chong-Chong Chen, Tao Yu, Jiayi Yang, Xiangdong Hu
Summary: Spiroxins A, C, and D are metabolites identified in the marine fungal strain LL-37H248, with unique polycyclic structures and intriguing biological activities. Researchers achieved the enantioselective total synthesis of (-)-spiroxins A and C, as well as the first total synthesis of (-)-spiroxin D, through a series of reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Martin Hebert, Gabriel Bellavance, Louis Barriault
Summary: Ginkgolides are compounds isolated from Ginkgo biloba that have anti-inflammatory and neuroprotective properties. This article reports the total synthesis of ginkgolide C and the formal syntheses of ginkgolides A and B, using a functional group strategy guided by the compact structure of ginkgolides.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Laura Burchill, Aaron J. Day, Oussama Yahiaoui, Jonathan H. George
Summary: Total synthesis of the Rhododendron meroterpenoids rubiginosins A and G, which possess unusual 6-6-6-4 ring systems, has been achieved using a bioinspired cascade approach. Stepwise synthesis of these natural products, and the related 6-6-5-4 meroterpenoids fastinoid B and rhodonoid B, from naturally occurring chromene precursors is also reported.
Article
Chemistry, Multidisciplinary
Xiu-Ning Hu, Dong-Ping Wu, Ye-Peng Xu, Pei-Qiang Huang
Summary: The first organocatalytic asymmetric synthesis of an advanced intermediate of (+)-sarain A was achieved by combining organocatalytic asymmetric Michael addition reaction and a nitrogen-to-carbon chirality transfer. This method allows for the construction of three chiral centers and chemoselective reduction of a key lactam intermediate, providing a tricyclic intermediate with all necessary functionalities for further elaboration into (+)-sarain A.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Dong-Huang Chen, Wei-Ting Sun, Cheng-Jie Zhu, Guang-Sheng Lu, Dong-Ping Wu, Ai-E Wang, Pei-Qiang Huang
Summary: The combination of transition-metal catalysis and organocatalysis has enabled chemists to achieve direct enantioselective reductive cyanation and phosphonylation of secondary amides, synthesizing enantioenriched chiral alpha-aminonitriles and alpha-aminophosphonates for the first time. The protocol is efficient, enantioselective, scalable, and the thiourea catalyst can be recycled and reused.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Ya-Qing Huang, Xiong-Zhi Huang, Pei-Qiang Huang
Summary: A two-step approach was developed for the synthesis of bicyclic and monocyclic 5-(1-alkoxyalkylidene)tetronates from lactones/esters, featuring the use of thionolactones and thionoesters as activated forms. This method was demonstrated to be valuable through the stereoselective synthesis of two natural products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Su-Yu Huang, Long-Hui Gao, Xiong-Zhi Huang, Pei-Qiang Huang
Summary: This article provides a detailed account of the synthetic efforts towards the enantioselective total synthesis of the complex alkaloid methoxystemofoline. The key steps include Keck allylation, olefin cross-metathesis, regioselective aldol addition, and Overman's method for moiety installation. The final step resulted in the formation of both the proposed structure of methoxystemofoline and its E-stereoisomer in a 1:1 ratio, leading to the suggestion to rename the natural product as isomethoxystemofoline.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Heng-Hui Li, Jia-Qi Li, Xiao Zheng, Pei-Qiang Huang
Summary: A decarboxylative cross-coupling reaction of alpha-amino acids with nitrones via visible-light-induced photoredox catalysis has been established, providing easy access to beta-amino hydroxylamines and vicinal diamines with structural diversity. This protocol offers efficient synthetic strategies for some valuable molecules containing vicinal diamine groups.
Article
Chemistry, Organic
Yi Lin, Shu-Fan He, Hui Geng, Yu-Chen Xiao, Kan-Lei Ji, Jian-Feng Zheng, Pei-Qiang Huang
Summary: A facile method for the preparation of 2,3-dialkylsubstituted quinazolinones from readily available N-arylamides and commercial isocyanates was developed, which involves the activation of the secondary amide with Tf2O/2-Br-Pyr, sequential addition of isocyanate, and cyclization. The mild reaction is general for a wide range of substrates and can be run on a gram scale.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Qian He, Jian-Liang Ye, Fang-Fang Xu, Hui Geng, Ting-Ting Chen, Hang Chen, Pei-Qiang Huang
Summary: The research findings demonstrated that Tf2O/TTBP can be an alternative amide activation system for the direct transformation of both secondary and tertiary amides, generally obtaining higher or comparable yields. Additionally, the combination of Tf2O/TTBP was also effective in promoting various important reactions, leading to concise and high-yield syntheses of natural products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Si-Jia Yu, Jian-Liang Ye, Ya-Cheng Hong, Pei-Qiang Huang
Summary: This paper describes the construction of functionalized and fused eight-membered carbocycles by triflic anhydride-mediated cyclization of 7-enamides. The reactions proceed smoothly to afford nonconjugated beta,gamma-enimines, conjugated alpha,beta-enimines, or fused 5/8 ring systems in good yields. Acidic hydrolysis of the cyclization reactions leads directly to the corresponding alpha,beta-enones, providing an efficient access to pendent cyclic beta,gamma-enimines/enones for some substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Dong-Ping Wu, Wei Ou, Pei-Qiang Huang
Summary: This study describes the catalytic reductive condensation reactions between tertiary amides and active methylene compounds, leading to multifunctionalized non-N-containing products. The reactions proceed through a sequential process involving iridium-catalyzed hydrosilylation of the amides followed by acid-mediated condensation with the active methylene compounds. This scalable method demonstrates a broad scope and remarkable chemoselectivity for the amide group in the presence of various sensitive or even more reactive functionalities such as ester, cyano, nitro, silyl dienol ether, and ketone.
Article
Multidisciplinary Sciences
Hang Chen, Zhi-Zhong Wu, Dong-Yang Shao, Pei-Qiang Huang
Summary: The catalytic asymmetric geminal bis-nucleophilic addition to nonreactive functional groups is a highly desirable yet challenging transformation in organic chemistry. In this study, the first catalytic asymmetric reductive/deoxygenative alkynylation of secondary amides was reported. The method combines iridium/copper relay catalysis with organocatalysis and allows the efficient synthesis of a variety of chiral a-branched amines. The protocol also demonstrates excellent enantioselectivity, chemoselectivity, and functional group tolerance.
Article
Chemistry, Multidisciplinary
Kan-Lei Ji, Shu-Fan He, Dong-Dong Xu, Wen-Xin He, Jian-Feng Zheng, Pei-Qiang Huang
Summary: A concise asymmetric total synthesis of (-)-quinocarcin has been achieved through high step economy using commercially available starting materials. The key chiral pyrrolidine intermediate with three stereocenters was prepared via a catalytic enantioselective reductive 1,3-dipolar cycloaddition reaction. This synthesis also involved a Rh-III-catalyzed C-H activation/cyclization and a tandem diastereoselective hydrogenation/cyclization to construct the tetrahydroisoquinoline-pyrrolidine tetracyclic core unit of quinocarcin.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Multidisciplinary Sciences
Fang-Fang Xu, Jin-Quan Chen, Dong-Yang Shao, Pei-Qiang Huang
Summary: The study presents a unified strategy for the synthesis of various alkaloids using readily available amides and alkynes, which is important for drug and agrochemical discovery.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Hang Chen, Dong-Huang Chen, Pei-Qiang Huang
Summary: This study demonstrates the catalytic intermolecular decarbamoylative C-C arylation and C-B borylation of N-acylpyrrole-based tertiary amides using nickel,N-heterocyclic carbene (NHC) catalysis. The research is significant for the direct transformation of amides.
CELL REPORTS PHYSICAL SCIENCE
(2023)
Article
Chemistry, Organic
Si-Jia Yu, Jie Li, Jian-Liang Ye, Pei-Qiang Huang
Summary: A one-pot reaction using palladium catalyst has been developed for the synthesis of bicyclic 1,3-oxazin-4-ones, 2,3,6,7-tetrahydrocyclopenta[e]-1,3-oxazin-4-ones and 2,3,5,6,7,8-hexahydro-4H-benzo[e]-1,3-oxazin-4-ones. The reaction shows good yields, broad substrate scope, mild reaction conditions, and scalability. It also demonstrates good compatibility with acetyl chloride and phenylacetyl chloride for the synthesis of monocyclic 1,3-oxazin-4-ones.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Hui-Rong Lu, Hui Geng, Guan-Tian Ding, Pei-Qiang Huang
Summary: We report a catalyst- and solvent-free method to synthesize enantioenriched secondary amides. The method is simple, mild, versatile, and efficient with high selectivity, and can be applied to different types of asymmetric products and alpha-branched primary amines.
