Strategies toward the total synthesis of pretubulysin, its fragments and analogues

References

• Sandmann, A.; Sasse, F.; Müller, R. Identification and Analysis of the Core Biosynthetic Machinery of Tubulysin, a Potent Cytotoxin with Potential Anticancer Activity. Chem. Biol. 2004, 11, 1071–1079. DOI: 10.1016/j.chembiol.2004.05.014.
   PubMedGoogle Scholar
• Kaur, G.; Hollingshead, M.; Holbeck, S.; Schauer-Vukašinović, V.; Camalier, R. F.; Dömling, A.; Agarwal, S. Biological Evaluation of Tubulysin A: A Potential Anticancer and Antiangiogenic Natural Product. Biochem. J. 2006, 396, 235–242. DOI: 10.1042/BJ20051735.
   PubMed Web of Science ®Google Scholar
• Iqbal, N.; Zahoor, A. F.; Rasool, N.; Khan, S. G.; Akhtar, R.; Ahmad, R. Synthetic Approaches Towards the Total Synthesis of Tubulysin and Its Fragments: A Review. Curr. Org. Synth. 2022, 19, 507-542. DOI: 10.2174/1570179419666211222163417.
   Google Scholar
• Ullrich, A.; Chai, Y.; Pistorius, D.; Elnakady, Y. A.; Herrmann, J. E.; Weissman, K. J.; Kazmaier, U.; Müller, R. Pretubulysin, a Potent and Chemically Accessible Tubulysin Precursor from Angiococcus disciformis. Angew. Chem. Int. Ed. Engl. 2009, 48, 4422–4425. DOI: 10.1002/anie.200900406.
   PubMed Web of Science ®Google Scholar
• Ullrich, A.; Herrmann, J.; Müller, R.; Kazmaier, U. Synthesis and Biological Evaluation of Pretubulysin and Derivatives. Eur. J. Org. Chem. 2009, 2009, 6367–6378. DOI: 10.1002/ejoc.200900999.
   Web of Science ®Google Scholar
• Herrmann, J.; Elnakady, Y. A.; Wiedmann, R. M.; Ullrich, A.; Rohde, M.; Kazmaier, U.; Vollmar, A. M.; Müller, R. Pretubulysin: From Hypothetical Biosynthetic Intermediate to Potential Lead in Tumor Therapy. PLoS One. 2012, 7, e37416. DOI: 10.1371/journal.pone.0037416.
   PubMed Web of Science ®Google Scholar
• Eirich, J.; Burkhart, J. L.; Ullrich, A.; Rudolf, G. C.; Vollmar, A.; Zahler, S.; Kazmaier, U.; Sieber, S. A. Pretubulysin Derived Probes as Novel Tools for Monitoring the Microtubule Network via Activity-Based Protein Profiling and Fluorescence Microscopy. Mol. Biosyst. 2012, 8, 2067–2075. DOI: 10.1039/C2MB25144B.
   PubMedGoogle Scholar
• Rath, S.; Liebl, J.; Fürst, R.; Ullrich, A.; Burkhart, J. L.; Kazmaier, U.; Herrmann, J.; Müller, R.; Günther, M.; Schreiner, L.; et al. Anti-Angiogenic Effects of the Tubulysin Precursor Pretubulysin and of Simplified Pretubulysin Derivatives. Br. J. Pharmacol. 2012, 167, 1048–1061. DOI: 10.1111/j.1476-5381.2012.02037.x.
   PubMed Web of Science ®Google Scholar
• Kretzschmann, V. K.; Gellrich, D.; Ullrich, A.; Zahler, S.; Vollmar, A. M.; Kazmaier, U.; Fürst, R. Novel Tubulin Antagonist Pretubulysin Displays Antivascular Properties In Vitro and In Vivo. Arterioscler. Thromb. Vasc. Biol. 2014, 34, 294–303. DOI: 10.1161/ATVBAHA.113.302155.
   PubMed Web of Science ®Google Scholar
• Brindisi, M.; Maramai, S.; Grillo, A.; Brogi, S.; Butini, S.; Novellino, E.; Campiani, G.; Gemma, S. Development of a Practical and Scalable Route for the Preparation of the Deacetoxytubuvaline (dTuv) Fragment of Pretubulysin and Analogs. Tetrahedron Lett. 2016, 57, 920–923. DOI: 10.1016/j.tetlet.2016.01.051.
   Web of Science ®Google Scholar
• Aditya, A.; Kodadek, T. Incorporation of Heterocycles into the Backbone of Peptoids to Generate Diverse Peptoid-Inspired One Bead One Compound Libraries. ACS Comb. Sci. 2012, 14, 164–169. DOI: 10.1021/co200195t.
   PubMed Web of Science ®Google Scholar
• Reddy, R. B.; Dudhe, P.; Chelvam, V. Synthesis of the Deacetoxytubuvaline Fragment of Pretubulysin and Its Lipophilic Analogues for Enhanced Permeability in Cancer Cell Lines. Synlett 2019, 30, 77–81. DOI: 10.1055/s-0037-1611359.
   Web of Science ®Google Scholar
• Menche, D.; Hassfeld, J.; Li, J.; Rudolph, S. Total Synthesis of Archazolid A. J. Am. Chem. Soc. 2007, 129, 6100–6101. DOI: 10.1021/ja071461o.
   PubMed Web of Science ®Google Scholar
• (a) Yadav, J. S.; Dutta, P. Total Synthesis of a Diacetonide Derivative of Thuggacin A. J. Org. Chem. 2016, 81, 1786–1797. DOI: 10.1021/acs.joc.5b02426.
   PubMed Web of Science ®Google Scholar
  (b) Facchinetti, V.; Avellar, M. M.; Nery, A. C. S.; Gomes, C. R. B.; Vasconcelos, T. R. A.; de Souza, M. V. N. An Eco-Friendly, Hantzsch-Based, Solvent-Free Approach to 2-Aminothiazole and 2-Aminoselenazoles. Synthesis 2016, 48, 437–440. DOI: 10.1055/s-0035-1560534.
   Web of Science ®Google Scholar
• Burkhart, J. L.; Müller, R.; Kazmaier, U. Syntheses and Evaluation of Simplified Pretubulysin Analogues. Eur. J. Org. Chem. 2011, 2011, 3050–3059. DOI: 10.1002/ejoc.201100155.
   Web of Science ®Google Scholar
• Dvornikovs, V.; Smithrud, D. B. Investigation of Synthetic Hosts That Model Cation-π Sites Found at Protein Binding Domains. J. Org. Chem. 2002, 67, 2160–2167. DOI: 10.1021/jo011124c.
   PubMed Web of Science ®Google Scholar
• Burkhart, J. L.; Kazmaier, U. A Straightforward Click-Approach Towards Pretubulysin-Analogues. RSC Adv. 2012, 2, 3785–3790. DOI: 10.1039/c2ra20191g.
   Web of Science ®Google Scholar
• Lei, H.; Stoakes, M. S.; Schwabacher, A. W.; Herath, K. P. B.; Lee, J. Efficient Synthesis of a Phosphinate Bis-Amino Acid and Its Use in the Construction of Amphiphilic Peptides. J. Org. Chem. 1994, 59, 4206–4210. DOI: 10.1021/jo00094a036.
   Web of Science ®Google Scholar
• Hoffmann, J.; Gorges, J.; Junk, L.; Kazmaier, U. Synthesis of Pretubulysin-Derivatives via the TubUgi-Approach. Org. Biomol. Chem. 2015, 13, 6010–6020. DOI: 10.1039/C5OB00587F.
   PubMedGoogle Scholar
• Nicolaou, K. C.; Yin, J.; Mandal, D.; Erande, R. D.; Klahn, P.; Jin, M.; Aujay, M.; Sandoval, J.; Gavrilyuk, J.; Vourloumis, D. Total Synthesis and Biological Evaluation of Natural and Designed Tubulysins. J. Am. Chem. Soc. 2016, 138, 1698–1708. DOI: 10.1021/jacs.5b12557.
   PubMed Web of Science ®Google Scholar
• Sohtome, Y.; Shin, B.; Horitsugi, N.; Takagi, R.; Noguchi, K.; Nagasawa, K. Entropy‐Controlled Catalytic Asymmetric 1,4‐Type Friedel-Crafts Reaction of Phenols Using Conformationally Flexible Guanidine/Bisthiourea Organocatalyst. Angew. Chem. Int. Ed. Engl. 2010, 49, 7299–7303. DOI: 10.1002/anie.201003172.
   PubMed Web of Science ®Google Scholar
• Nicolaou, K. C.; Erande, R. D.; Yin, J.; Vourloumis, D.; Aujay, M.; Sandoval, J.; Munneke, S.; Gavrilyuk, J. Improved Total Synthesis of Tubulysins and Design, Synthesis, and Biological Evaluation of New Tubulysins With Highly Potent Cytotoxicities Against Cancer Cells as Potential Payloads for Antibody-Drug Conjugates. J. Am. Chem. Soc. 2018, 140, 3690–3711. DOI: 10.1021/jacs.7b12692.
   PubMed Web of Science ®Google Scholar