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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 5
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Articles

Synthesis of tubuvaline (Tuv) fragment of tubulysin via diastereoselective dihydroxylation of homoallylamine

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Pages 797-809 | Received 12 Oct 2020, Published online: 07 Dec 2020

References

  • Jordan, M. A.; Wilson, L. Microtubules as a Target for Anticancer Drugs. Nat. Rev. Cancer 2004, 4, 253–265. DOI: 10.1038/nr1317. DOI: 10.1038/nrc1317.
  • Khalil, M. W.; Sasse, F.; Lünsdorf, H.; Elnakady, Y. A.; Reichenbach, H. Mechanism of Action of Tubulysin, an Antimitotic Peptide from Myxobacteria. Chembiochem 2006, 7, 678–683. DOI: 10.1002/cbic.200500421.
  • 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.
  • 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.
  • Pando, O.; Dörner, S.; Preusentanz, R.; Denkert, A.; Porzel, A.; Richter, W.; Wessjohann, L. First Total Synthesis of Tubulysin B. Org. Lett. 2009, 11, 5567–5569. DOI: 10.1021/ol902320w.
  • Peltier, H. M.; McMahon, J. P.; Patterson, A. W.; Ellman, J. A. The Total Synthesis of Tubulysin D. J. Am. Chem. Soc. 2006, 128, 16018–16019. DOI: 10.1021/ja067177z.
  • Sasse, F.; Steinmetz, H.; Heil, J.; Höfle, G.; Reichenbach, H. Tubulysins, New Cytostatic Peptides from Myxobacteria Acting on Microtubuli. Production, Isolation, Physico-Chemical and Biological Properties. J. Antibiot. 2000, 53, 879–885. DOI: 10.7164/antibiotics.53.879.
  • Murray, B. C.; Peterson, M. T.; Fecik, R. A. Chemistry and Biology of Tubulysins: Antimitotic Tetrapeptides with Activity against Drug Resistant Cancers. Nat. Prod. Rep. 2015, 32, 654–662. DOI: 10.1039/c4np00036f.
  • 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.
  • Steinmetz, H.; Glaser, N.; Herdtweck, E.; Sasse, F.; Reichenbach, H.; Höfle, G. Isolation, Crystal and Solution Structure Determination, and Biosynthesis of Tubulysins-Powerful Inhibitors of Tubulin Polymerization from Myxobacteria. Angew. Chem. Int. Ed. Engl. 2004, 43, 4888–4892. DOI: 10.1002/anie.200460147.
  • 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.
  • Wipf, P.; Wang, Z. Total Synthesis of N14-Desacetoxytubulysin H. Org. Lett. 2007, 9, 1605–1607. DOI: 10.1021/ol070415q.
  • Raghavan, B.; Balasubramanian, R.; Steele, J. C.; Sackett, D. L.; Fecik, R. A. Cytotoxic Simplified Tubulysin Analogues. J. Med. Chem. 2008, 51, 1530–1533. DOI: 10.1021/jm701321p.
  • Balasubramanian, R.; Raghavan, B.; Begaye, A.; Sackett, D. L.; Fecik, R. A. Total Synthesis and Biological Evaluation of Tubulysin U, Tubulysin V, and Their Analogues. J. Med. Chem. 2009, 52, 238–240. DOI: 10.1021/jm8013579.
  • Wipf, P.; Takada, T.; Rishel, M. J. Synthesis of the Tubuvaline-Tubuphenylalanine (Tuv-Tup) Fragment of Tubulysin. Org. Lett. 2004, 6, 4057–4060. DOI: 10.1021/ol048252i.
  • Chandrasekhar, S.; Mahipal, B.; Kavitha, M.; Toward Tubulysin: Gram-Scale Synthesis Of Tubuvaline-Tubuphenylalanine FragmentChandrasekhar, S.; Mahipal, B.; Kavitha, M. Toward Tubulysin: Gram-Scale Synthesis of Tubuvaline-Tubuphenylalanine Fragment. J. Org. Chem. 2009, 74, 9531–9534. 2009,DOI: 10.1021/jo9015503.
  • Reddy, R. B.; Dudhe, P.; Chauhan, P.; Sengupta, S.; Chelvam, V. Synthesis of Tubuphenylalanine and Epi-Tubuphenylalanine via Regioselective Aziridine Ring Opening with Carbon Nucleophiles Followed by Hydroboration-Oxidation of 1,1-Substituted Amino Alkenes. Tetrahedron 2018, 74, 6946–6953. DOI: 10.1016/j.tet.2018.10.024.
  • 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.
  • Wang, Z.; McPherson, P. A.; Raccor, B. S.; Balachandran, R.; Zhu, G.; Day, B. W.; Vogt, A.; Wipf, P. Structure-Activity and High-Content Imaging Analyses of Novel Tubulysins. Chem. Biol. Drug Des. 2007, 70, 75–86. DOI: 10.1111/j.1747-0285.2007.00541.x.
  • Balasubramanian, R.; Raghavan, B.; Steele, J. C.; Sackett, D. L.; Fecik, R. A. Tubulysin Analogs Incorporating Desmethyl and Dimethyl Tubuphenylalanine Derivatives. Bioorg. Med. Chem. Lett. 2008, 18, 2996–2999. DOI: 10.1016/j.bmcl.2008.03.046.
  • Shibue, T.; Hirai, T.; Okamoto, I.; Morita, N.; Masu, H.; Azumaya, I.; Tamura, O. Total Syntheses of Tubulysins. Chemistry 2010, 16, 11678–11688. DOI: 10.1002/chem.201000963.
  • Shibue, T.; Okamoto, I.; Morita, N.; Morita, H.; Hirasawa, Y.; Hosoya, T.; Tamura, O. Synthesis and Biological Evaluation of Tubulysin D Analogs Related to Stereoisomers of Tubuvaline. Bioorg. Med. Chem. Lett. 2011, 21, 431–434. DOI: 10.1016/j.bmcl.2010.10.118.
  • Shankar, P. S.; Bigotti, S.; Lazzari, P.; Manca, I.; Spiga, M.; Sani, M.; Zanda, M. Synthesis and Cytotoxicity Evaluation of Diastereoisomers and N-Terminal Analogues of Tubulysin-U. Tetrahedron Lett. 2013, 54, 6137–6141. DOI: 10.1016/j.tetlet.2013.09.010.
  • Shankar, S. P.; Jagodzinska, M.; Malpezzi, L.; Lazzari, P.; Manca, I.; Greig, I. R.; Sani, M.; Zanda, M. Synthesis and Structure-Activity Relationship Studies of Novel Tubulysin U Analogues-Effect on Cytotoxicity of Structural Variations in the Tubuvaline Fragment. Org. Biomol. Chem. 2013, 11, 2273–2287. DOI: 10.1039/c3ob27111k.
  • Trabocchi, A.; Guarna, F.; Guarna, A. γ- and δ-Amino Acids: Synthetic Strategies and Relevant Applications. Coc. 2005, 9, 1127–1153. DOI: 10.2174/1385272054553631.
  • Ordóñez, M.; Cativiela, C. Stereoselective Synthesis of γ-Amino Acids. Tetrahedron: Asymmetry 2007, 18, 3–99. DOI: 10.1016/j.tetasy.2006.12.001.
  • Schroeder, M. Osmium Tetraoxide Cis Hydroxylation of Unsaturated Substrates. Chem. Rev. 1980, 80, 187–213. DOI: 10.1021/cr60324a003.
  • Torii, S.; Liu, P.; Bhuvaneswari, N.; Amatore, C.; Jutand, A. Chemical and Electrochemical Asymmetric Dihydroxylation of Olefins in I(2)-K(2)CO(3)-K(2)OsO(2)(OH)(4) and I(2)-K(3)PO(4)/K(2)HPO(4)-K(2)OsO(2)(OH)(4) Systems with Sharpless' Ligand. J. Org. Chem. 1996, 61, 3055–3060. DOI: 10.1021/jo952137r.
  • Bolm, C.; Gerlach, A. Polymer-Supported Catalytic Asymmetric Sharpless Dihydroxylations of Olefins. Eur. J. Org. Chem. 1998, 1998, 21–27. DOI: 10.1002/(SICI)1099-0690(199801)1998:1<21::AID-EJOC21>3.0.CO;2-0.
  • Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Catalytic Asymmetric Dihydroxylation. Chem. Rev. 1994, 94, 2483–2547. DOI: 10.1021/cr00032a009.
  • Tanner, D. Chiral Aziridines-Their Synthesis and Use in Stereoselective Transformations. Angew. Chem. Int. Ed. Engl. 1994, 33, 599–619. DOI: 10.1002/anie.199405991.
  • McCoull, W.; Davis, F. A. Recent Synthetic Applications of Chiral Aziridines. Synthesis 2000, 2000, 1347–1365. DOI: 10.1055/s-2000-7097.
  • Berry, M. B.; Craig, D. A Convenient Method for the Preparation of Enantiomerically Pure 2-Substituted N-Tosylaziridines. Synlett 1992, 1992, 41–44. DOI: 10.1055/s-1992-21259.
  • Dogan, O.; Polat-Cakir, S. Recent Progress in Asymmetric Synthesis of Aziridine Derivatives. Chem. Heterocycl. Comp. 2018, 54, 397–399. DOI: 10.1007/s10593-018-2282-2.
  • 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.

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