The Chemistry of Ynamide and Its Application in Organic Synthesis
Siyu Ye, Na Wu (2020) Advances in Organic Synthesis. Bentham Science Publishers.
Dr. Na (also Anna) Wu has embarked on an international journey to pursue her research career. She studied organic synthesis first at the Shann’xi Normal University (BS in Chemistry) and then at Peking University (2006-2010, MS & Ph.D. in Synthesis & Catalysis, emphasizing the use of Pauson-Khand reaction (PKR) in the total synthesis of (±)-Pentalenolactone-a Methyl Ester) with Prof. Zhen Yang, formally graduating in June 2012. Anna was a visiting researcher at Durham University from 2010-11, hosted by Prof Todd Marder where she studied palladium-thiourea catalyzed enyne domino reactions. This was followed by a postdoctoral research assistant position with Prof. Simon Woodward at University of Nottingham in 2013, where she studied the trichloromethide addition mechanism. She held the Research Fellowship at Guangxi Normal University in 2015. In 2018, Anna was awarded the prestigious Royal Society Newton International Research Fellowship to work at the University of Oxford under the supervision of Prof. Edward Anderson. Anna came to Durham University in June 2018 to continue the fellowship under the supervision of Prof. Andy Whiting. In 2020, she takes up the position of Lecturer in Bioorganic Chemistry at the University of Bradford, which allows her to start an independent research on organic synthesis and catalysis.
Dr. Wu is the recipient of national and international awards and research grants: UK-China joint training doctoral students scholarship awarded by CSC (Chinese Scholarship Council), 2010-2011, Guangxi Province Key Laboratory grant, 2014-2017, Research Grant awarded by National Nature Science Foundation of China, 2015-2018, Young Investigator Research Grant awarded by Guangxi Provincial Nature Science Foundation, 2015-2017, Research Grant from Peking University Shenzhen graduate school, 2016, Newton International Research Fellowship, awarded by the UK Royal Society, Marie Sklodowska-Curie Actions Seal of Excellence, awarded by European Commission, 2018. She is also a member of the RSC.
For full publications, see https://orcid.org/0000-0003-1668-6652
1. To design 'domino' strategies which enable the formation of multiple bonds in a single step, and to explore new domino reactions in palladium catalysis, which are connected by the principle of reaction initiation through nucleopalladation to access polycyclic alkaloids as bioactive agents.
1.1 Palladium-catalysed enantioselective enyne cyclisations to form quaternary stereocenters via asymmetric counterion directed catalysis: Application of Dehydroabietic Acid in Palladium-Catalysed Enyne Cycloisomerisation, Na Wu*, Ruikun Li, Feihu Cui and Yingming Pan, Adv. Synth. Catal., 2017, 359(14), 2442.
1.2 Pauson-Khand reactions (PKR) to form substituted cyclopentenones as found in complex natural products: Highly Stereoselective Construction of the Framework of Pentalenolactone: First Total Synthesis of (±)-Pentalenolactone A Methyl Ester, Qi Liu, Guozong Yue, Na Wu, Guang Lin, Yuanzhen Li, Chuangchuang Li, Junmin Quan, Guoxin Wang and Zhen Yang*, Angew. Chem. Int. Ed., 2012, 51, 12072. Top 10 Most Accessed Article in October, 2012.Highlighted in Chin. J. Org. Chem., January, 2013.Highlighted in Chemistry World, November, 2012.
1.3 Mechanistic studies in palladium-catalysed Pauson-Khand reactions initiated by alkynoate chloropalladation rather than the conventional cyclometallation pathway; Control of Pauson-Khand reactions regioselectivity using lithium halide salts: Reverse Regioselectivity in the Pd(II)-Thiourea Catalyzed Intermolecular Pauson-Khand Reaction, Na Wu, Lujiang Deng, Lianzhu Liu, Qi Liu, Chuangchuang Li and Zhen Yang*, Chem. Asian. J., 2013, 8 (1), 65.
1.4 Enyne cycloisomerisation / Diels-Alder reaction / alkoxycarbonylation / lactonisation sequences as atom economic routes to afford fused carbocyclic lactones:
Application of Dehydroabietic Acid in Palladium-Catalysed Enyne Cycloisomerisation, Na Wu*, Ruikun Li, Feihu Cui and Yingming Pan, Adv. Synth. Catal., 2017, 359(14), 2442.
TfOH-Catalyzed Reaction of Bispropargyl Alcohols with 1,3-Dicarbonyl Compounds, Qing-hu Teng, Shi-kun Mo, Jian-kun Pan, Na Wu,* Heng-shan Wang and Ying-ming Pan*, Synthesis, 2016, 3, 455.
Highlighted in ChemInform., 2016, 47 (25), DOI: 10.1002/chin.201625089.
Atom-economical Chemoselective Synthesis of Furocoumarins via Cascade Palladium Catalyzed Oxidative Alkoxylation of 4-Oxohydrocoumarins and Alkenes, Xian-chun Tan, Hai-yuan Zhao, Ying-ming Pan,* Na Wu, Heng-Shan Wang and Zhen-feng Chen*, RSC Adv., 2015, 5, 4972.
Highlighted in ChemInform., 2015, 46 (24), DOI: 10.1002/chin.201524163
A Model Study for the Concise Construction of the Oxapentacyclic Core of Cortistatins through Intramolecular Diels-Alder and Oxidative Dearomatization-Cyclization Reactions, Lianzhu Liu, Yingxiang Gao, Chao Che, Na Wu, David ZhigangWang, ChuangChuang Li and Zhen Yang*, Chem. Commun., 2009, 6, 662. Highlighted in ChemInform, 2009, 40, DOI: 10.1002/chin.200925181.
Unexpected Regioselectivity in the Synthesis of Pyranonaphthoquinone via the Diels-Alder Reaction, Yi Cui, Hao Jiang, Zhengtao Li, Na Wu, Zhen Yang* and Junmin Quan, Org. Lett., 2009, 11, 4628.
Diversity-Oriented Synthesis of Fused Pyran γ-Lactones via an Efficient Pd-Thiourea-Catalyzed Alkoxycarbonylative Annulation, Zhengtao Li, Yingxiang Gao, Zhaodong Jiao, Na Wu, David Zhigang Wang and Zhen Yang*, Org. Lett., 2008, 10, 5163. Highlighted by Mark Lautens, David A. Candito. Synfacts 2009, 2, 0188.
1.5 Electron-reverse reductive Heck cyclisation (Hydroarylation) of en-ynamide to indoles / hydride migration: Palladium-Catalysed Ligand-Free Reductive Heck Cycloisomerisation of 1,6-En-α-chloro-enamides, Yangyang Hou, Jing Ma, Hongyi Yang, Andy Whiting, Edward A. Anderson and Na Wu*, Chem. Commun., 2019, 55, 3733.
1.6 Wagner-Meerwein-type rearrangements of en-ynones to access polycyclic pyrones, model synthesis of nodulisporic acid and taiwaniaquinol: Palladium(II)-Catalyzed Tandem Cyclisation of Electron-Deficient Aromatic Enynes, Na Wu, Antonios Messinis, Andrei S. Batsanov, Zhen Yang, Andrew Whiting and Todd. B. Marder*, Chem. Commun., 2012, 48 (80), 9986. Highlighted in ChemInform., 2013, 44, DOI: 10.1002/chin.201303035. Highlighted by Synfacts 2012, 8 (12), 1295.
An Irreversible Phase Transition in 1-n-butylindeno[2,1-c]pyran-3,9-dione, Andrei S. Batsanov*, Judith A. K. Howard, Na Wu, Zhen Yang and Todd B. Marder, Acta Cryst., 2012, C68, o413.
1.7 Synthesis of β-enaminoketoesters via “masked” 1,3-aza-dipoles cascade rearrangements: One-Pot Stepwise Approach to β-Enaminoketoesters through “Masked” 1,3-Aza-Dipoles, Zhi-ming Yan, Na Wu*, Dong Liang, Heng-shan Wang and Ying-ming Pan*, Org. Lett., 2014, 16, 4048. Highlighted in ChemInform., 2015, 46 (4), DOI: 10.1002/chin.201504054
1.8 Developing new chiral dienes from extracts of plants for use in rhodium catalysis:
Nordehydroabietyl Amide-Containing Chiral Diene for Rhodium-Catalysed Asymmetric Arylation to Nitroolefins, Ruikun Li, Zhongqing Wen and Na Wu*, Org. Biol. Chem., 2016, 14, 11080.
1.9 Mechanistic study of racemic and asymmetric nucleophilic addition of trichloromethanide to Michael acceptors: 1,4-Addition of TMSCCl3 to Nitroalkenes: Efficient Reaction Conditions and Mechanistic Understanding, Na Wu, Benoit Wahl, Simon Woodward* and William Lewis, Chem. Eur. J., 2014, 20, 7718. Highlighted in ChemInform., 2014, 45 (51), DOI: 10.1002/chin.201451026
2. To synthesize useful building blocks ynamides and ynamines, as well as their utilisation into delivering light-harvesting and fluorescent materials.
2.1 To develop an easy-to-handle, ready-to-scale-up method that would be attractive in industry to access diversified ynamides and ynamines, via copper-free Sonogashira coupling reaction in water. The currently environmentally-friendly simple route allows for large scale preparation of ynamides, and further, providing a practical perspective on the de novo synthesis of complex natural product-based ynamides. Synthesis of Sulfonamide-Based Ynamides and Ynamines in Water, Lei Zhao, Hongyi Yang, Ruikun Li, Ye Tao, Xiao-Feng Guo, Edward A. Anderson, Andy Whiting and Na Wu*, , 2021, 86(2), 1938.
Highlighted by Organic Chemistry Portal as useful chemistry: https://www.organic-chemistry.org/abstracts/lit7/743.shtm
Highlighted by Chin. J. Chem. 2023, 41, 1099-1118.
2.2 The Chemistry of Ynamide and Its Application in Organic Synthesis, Siyu Ye and Na Wu*, eds: A. Rahma, Advances in Organic Synthesis, 13th ed. Bentham: the Netherlands, 2020, 13(2), 52-170.
2.3 Functionalisation of ynamides / ynamines with iodonium salts to afford acyloxyl amide. Metal-Free Oxyacetoxylation of Arylynamines and Ynamides to Construct α-Acetoxyl Amides, Rong Long, Shaoling Huang, Han-Kui Wu, Naila Iqbal and Na Wu*, Eur. J. Org. Chem., 2023, DOI: 10.1002/ejoc.202300393.
2.4 Synthesis of Orthogonal Push-Pull Chromophores via Click Reaction of Arylynamines, Shuangping Huang, Jing Ma, Yikun Yi, Mingtao Li, Ping Cai and Na Wu*, Org. Biomol. Chem., 2022, 20, 4081.
Key words: palladium, copper catalysis, dipolar cycloaddition, metal-free enyne cyclisation.
opportunities to join us:
Schlumberger faculty for the future:
https://www.fftf.slb.com/
Commonwealth PhD scholarship, master scholarship:
https://lnkd.in/gcxWdSCN
Chinese Scholarship Council visiting scholarship:
https://lnkd.in/gyKcAcZ4
Nigerian Tertiary Fund Trust: https://tetfund.gov.ng/index.php/guideline-10/
Siyu Ye, Na Wu (2020) Advances in Organic Synthesis. Bentham Science Publishers.
Shuangping Huang, Jing Ma, Yikun Yi, Mingtao Li, Ping Cai and Na Wu* (2022) Org Biomol Chem. 20
Li, X; Wang, G; Zhang, Z; Wu, Na; Yang, Q; Huang, S; Wang, X (2019) Synthetic Communications. 49
Hou, Y; Ma, J; Yang, H; Anderson, EA; Whiting, A; Wu Na (2019) Chemical Communications (Cambridge, England). 55
Deng, J; Yu, P; Zhang, Z; Wang, J; Cai, J; Wu, Na; Sun, W; Liang, H; Yang, F (2018) European Journal of Medicinal Chemistry. 158
Wu, N; Li, R; Cui, F; Pan, Y (2017) Advanced Synthesis and Catalysis. 359, 2442-2447.
Teng, Q; Mo, S; Pan, J; Wu, Na; Wang, H; Pan Y (2016) Synthesis. 48
Li, R; Wen, Z; Wu, Na (2016) Organic and Biomolecular Chemistry. 14
Tan, X; Zhao, H; Pan, Y; Wu, Na; Wang, H; Chen, Z (2015) RSC Advances. 5, 4972-4975.
Wu, Na; Wahl, B; Woodward, S; Lewis, W (2014) Chemistry - A European Journal. 20, 7718-7724.
Yan ZM;Wu N;Liang D;Wang HS;Pan YM; (2014) Organic Letters. 16
Wu N;Deng L;Liu L;Liu Q;Li C;Yang Z; (2013) Chemistry - An Asian Journal. 8
Batsanov AS;Howard JA;Wu N;Yang Z;Marder TB; (2012) Acta Crystallographica Section C: Crystal Structure Communications. 68
Wu N;Messinis A;Batsanov AS;Yang Z;Whiting A;Marder TB; (2012) Chemical Communications. 48
Liu Q;Yue G;Wu N;Lin G;Li Y;Quan J;Li CC;Wang G;Yang Z; (2012) Angewandte Chemie - International Edition. 51
Liu L.;Gao Y.;Che C.;Wu N.;Wang D.Z.;Li C.C.;Yang Z. (2009) Chemical Communications., 662-664.
Cui Y;Jiang H;Li Z;Wu N;Yang Z;Quan J; (2009) Organic Letters. 11
Li Z;Gao Y;Jiao Z;Wu N;Wang DZ;Yang Z; (2008) Organic Letters. 10