Total synthesis of (±)-coerulescine and (±)-horsfiline

Scholarly Works

• Javahershenas, R.; Makarem, A.; Klika, K. D. Recent advances in microwave-assisted multicomponent synthesis of spiro heterocycles. RSC advances 2024, 14, 5547–5565. doi:10.1039/d4ra00056k
• V, R. N.; Gamidi, R. K.; Kumari, J.; Sri, D.; Basavoju, S. A Green one-pot three component synthesis of thiazolidine-2,4-dione based bisspirooxindolo-pyrrolidines with [Bmim]BF 4 : their in vitro and in silico anti- TB studies. Research Square Platform LLC 2024. doi:10.21203/rs.3.rs-3920729/v1
• Sephton, T.; Large, J. M.; Butterworth, S.; Greaney, M. F. Synthesis of Functionalized Pyrrolidinone Scaffolds via Smiles-Truce Cascade. Organic letters 2023, 25, 6736–6740. doi:10.1021/acs.orglett.3c02559
• Yang, L.; Hou, A.; Jiang, Q.; Cheng, M.; Liu, Y. Methodological Development and Applications of Tryptamine-Ynamide Cyclizations in Synthesizing Core Skeletons of Indole Alkaloids. The Journal of organic chemistry 2023, 88, 11377–11391. doi:10.1021/acs.joc.3c01088
• Zhan, D.; Yao, B.; Huan, C.; Lu, J.; Ji, Y.; Zhang, X. A step-economical and diastereoselective synthesis of dispirooxindole-pyrrolizines bearing seven stereocenters. Tetrahedron Letters 2023, 126, 154638. doi:10.1016/j.tetlet.2023.154638
• Sahu, N. K.; Sharma, R.; Suhas, K. P.; Joshi, J.; Prakash, K.; Sharma, R.; Pratap, R.; Hu, X.; Kaur, S.; Jain, M.; Coluccini, C.; Coghi, P.; Chaudhary, S. Natural-Product-Inspired Microwave-Assisted Synthesis of Novel Spirooxindoles as Antileishmanial Agents: Synthesis, Stereochemical Assignment, Bioevaluation, SAR, and Molecular Docking Studies. Molecules (Basel, Switzerland) 2023, 28, 4817. doi:10.3390/molecules28124817
• Bhat, A. A.; Singh, I.; Tandon, N.; Tandon, R. Structure activity relationship (SAR) and anticancer activity of pyrrolidine derivatives: Recent developments and future prospects (A review). European journal of medicinal chemistry 2022, 246, 114954. doi:10.1016/j.ejmech.2022.114954
• Moghaddam, F. M.; Hosseinzadeh, N.; Fazli, H.; Sadredini, S.; Foroumadi, A. Regio- and Stereoselective Synthesis of Dispiropyrrolidineoxindole Derivatives by Using Classical and Microwave Conditions, and Molecular Docking Studies of Them as Potential Cyclin Dependent Kinases (CDK5) Inhibitors. Polycyclic Aromatic Compounds 2022, 43, 6898–6910. doi:10.1080/10406638.2022.2127801
• Barakat, A.; Haukka, M.; Soliman, S. M.; Al-Majid, A. M.; Ali, M.; Islam, M. S.; Karami, A. M.; Ul-Haq, Z.; Domingo, L. R. Synthesis and anti-Cancer Activity of a New Hybrid Based Spirooxindole-Pyrrolidine -Thiochromene Scaffolds via [3 + 2] Cycloaddition Reaction: Computational Investigation. Polycyclic Aromatic Compounds 2022, 43, 2302–2320. doi:10.1080/10406638.2022.2042334
• Zhang, X.; Qiu, W.; Murray, S. A.; Zhan, D.; Evans, J.; Jasinski, J. P.; Wang, X.; Zhang, W. Pseudo-Five-Component Reaction for Diastereoselective Synthesis of Butterfly Shaped Bispiro[Oxindole-Pyrrolidine]s. The Journal of organic chemistry 2021, 86, 17395–17403. doi:10.1021/acs.joc.1c01797
• Sakthivel, P.; Sudalai, A. doi:10.1002/047084289x.rn02426
• Kumar, P. P. S.; Krishnaswamy, G.; Desai, N. R.; Sreenivasa, S.; Kumar, D. B. A. Highly Facile, Regio- and Stereoselective Synthesis of Spiropyrrolidine-5-aza-2-oxindole Derivatives through Multicomponent 1,3-Dipolar Cycloaddition Reaction and Their In-Vitro and In-Silico Biological Studies. ChemistrySelect 2021, 6, 9407–9414. doi:10.1002/slct.202102118
• Bhattacharya, A.; Thirupathi, A.; Natarajan, P.; Peruncheralathan, S. Chemoselective Ullmann Reaction of α-Trisubstituted Thioamides: Synthesis of Novel 2-Iminobenzothiolanes. ACS omega 2021, 6, 21169–21180. doi:10.1021/acsomega.1c03410
• Sathish, M.; Sakla, A. P.; Nachtigall, F. M.; Santos, L. S.; Shankaraiah, N. TCCA-mediated oxidative rearrangement of tetrahydro-β-carbolines: facile access to spirooxindoles and the total synthesis of (±)-coerulescine and (±)-horsfiline. RSC advances 2021, 11, 16537–16546. doi:10.1039/d1ra02381k
• Sharma, V.; Begam, S.; Nurjamal, K.; Brahmachari, G.; Gupta, V. K. Synthesis, Characterization, and Crystal Structure of [3,3':3',3''-Terindolin]-2'-One Bis(dimethyl Sulfoxide). Crystallography Reports 2020, 65, 1187–1190. doi:10.1134/s1063774520070159
• Sathish, M.; Nachtigall, F. M.; Santos, L. S. Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-β-carbolines and enantioselective synthesis of (-)-coerulescine and (-)-horsfiline by oxidative rearrangement. RSC advances 2020, 10, 38672–38677. doi:10.1039/d0ra07705d
• Heravi, M. M.; Zadsirjan, V.; Hamidi, H.; Daraie, M.; Momeni, T. Recent applications of the Wittig reaction in alkaloid synthesis. The Alkaloids. Chemistry and biology 2020, 84, 201–334. doi:10.1016/bs.alkal.2020.02.002
• Zhou, L.-M.; Qu, R.-Y.; Yang, G.-F. An overview of spirooxindole as a promising scaffold for novel drug discovery. Expert opinion on drug discovery 2020, 15, 603–625. doi:10.1080/17460441.2020.1733526
• Nurjamal, K.; Brahmachari, G. Sodium Formate-Catalyzed One-Pot Synthesis of Functionalized Spiro[indoline-3,5′-pyrido[2,3-d]pyrimidine]/Spiro[acenaphthylene-1,5′-pyrido[2,3-d]-pyrimidine] Derivatives. ChemistrySelect 2019, 4, 2363–2367. doi:10.1002/slct.201803508
• Chen, C.; Xu, L.; Wang, L.; Li, S.-S. Efficient construction of tetrahydroquinolines via fluorinated alcohol mediated cascade [1,5]-hydride transfer/cyclization. Organic & biomolecular chemistry 2018, 16, 7109–7114. doi:10.1039/c8ob02012d

Explore citations to this article at