Total synthesis of (–)-negamycin from a chiral advanced epoxide

References

• (a) van Heijenoort, J. Recent Advances in the Formation of the Bacterial Peptidoglycan Monomer Unit. Nat. Prod. Rep. 2001, 18, 503–519. DOI: 10.1039/a804532a. (b) Breukink, E.; de Kruijff, B. Lipid II as a Target for Antibiotics. Nat. Rev. Drug Discov. 2006, 5, 321–332. (c) Bugg, T. D. H.; Braddick, D.; Dowson, C. G.; Roper, D. I. Bacterial Cell Wall Assembly: Still an Attractive Antibacterial Target. Trends Biotechnol. 2011, 29, 167–173. (d) Typas, A.; Banzhaf, M.; Gross, C. A.; Vollmer, W. From the Regulation of Peptidoglycan Synthesis to Bacterial Growth and Morphology. Nat. Rev. Microbiol. 2012, 10, 123–136.(e) Cava, F.; de Pedro, M. A. Peptidoglycan Plasticity in Bacteria: Emerging Variability of the Murein Sacculus and Their Associated Biological Functions. Curr. Opin. Microbiol. 2014, 18, 46–53.
   PubMed Web of Science ®Google Scholar
• Hamada, M.; Takeuchi, T.; Kondo, S.; Ikeda, Y.; Naganawa, H.; Maeda, K.; Okami, Y.; Umezawa, H. A New Antibiotic, Negamycin. J. Antibiot. 1970, 23, 170–171. DOI: 10.7164/antibiotics.23.170.
   PubMed Web of Science ®Google Scholar
• Kondo, S.; Shibahara, S.; Takahashi, S.; Maeda, K.; Umezawa, H. Negamycin, a Novel Hydrazide Antibiotic. J. Am. Chem. Soc. 1971, 93, 6305–6306. DOI: 10.1021/ja00752a072.
   PubMed Web of Science ®Google Scholar
• Shibahara, S.; Kondo, S.; Maeda, K.; Umezawa, H.; Ono, M. The Total Syntheses of Negamycin and the Antipode. J. Am. Chem. Soc. 1972, 94, 4353–4354. DOI: 10.1021/ja00767a059.
   PubMed Web of Science ®Google Scholar
• (a) A review paper related total synthesis of negamycin Zhu, L.; Hong, R, Pursuing Effective Gram-Negative Antibiotics: The Chemical Synthesis of Negamycin. Tetrahedron Lett. 2018, 59, 2112–2127 and references therein. DOI: 10.1016/j.tetlet.2018.04.059. (b) Zhang, S.; Li, X.; Wang, Y.; Zheng, Y.; Han, S.; Yu, H.; Huang, S. Formal Synthesis of Gram-Negative Antibiotic Negamycin. Chin. J. Org. Chem. 2020, 40, 521–527.
   Web of Science ®Google Scholar
• (a) Davies, S. G.; Ichihara, O. Asymmetric Synthesis of (+)-Negamycin. Tetrahedron: Asymmetry 1996, 7, 1919–1922. DOI: 10.1016/0957-4166(96)00230-3. (b) Davies, S. G.; Ichihara, O.; Roberts, P. M.; Thomson, J. E. Asymmetric Syntheses of (+)-Negamycin, (+)-3-Epi-Negamycin and Sperabillin C via Lithium Amide Conjugate Addition. Tetrahedron 2011, 67, 216–227.
   Web of Science ®Google Scholar
• (a) Hayashi, Y.; Regnier, T.; Nishiguchi, S.; Sydnes, M. O.; Hashimoto, D.; Hasegawa, J.; Katoh, T.; Kajimoto, T.; Shiozuka, M.; Matsuda, R.; et al. Efficient Total Synthesis of (+)-Negamycin, a Potential Chemotherapeutic Agent for Genetic Diseases. Chem. Commun. 2008, 2379–2381. DOI: 10.1039/b801498a. (b) Nishiguchi, S.; Sydnes, M. O.; Taguchi, A.; Regnier, T.; Kajimoto, T.; Node, M.; Yamazaki, Y.; Yakushiji, F.; Kiso, Y.; Hayashi, Y. Total Synthesis of (+)-Negamycin and Its 5-Epi-Derivative. Tetrahedron 2010, 66, 314–320.
   Web of Science ®Google Scholar
• Lin, C.-K.; Hsieh, B.-H.; Wu, C.-F. Total Synthesis of Citreochlorol Monochloro Analogues via a Catalytically Enantioselective Carbonyl Allylation. Synthesis 2022, 54, 1321–1328. DOI: 10.1055/a-1669-0463.
   Web of Science ®Google Scholar
• (a) Cossy, J.; Pradaux, F.; BouzBouz, S. Synthesis of the C1–C12 Fragment of Fostriecin. Org. Lett. 2001, 3, 2233–2235. DOI: 10.1021/ol016116x. (b) Yan, X.; Zhang, S.-M.; Wu, Y.; Gao, P. Synthesis and Configuration of the Nonadecenetriol Isolated from Seeds of Persea americana. Org. Biomol. Chem. 2011, 9, 6797–6806. (c) Alam, M.; Wise, C.; Baxter, C. A.; Cleator, E.; Walkinshaw, A. Development of a Robust Procedure for the Copper-Catalyzed Ring-Opening of Epoxides with Grignard Reagents. Org. Process Res. Dev. 2012, 16, 435–441.(d) Chen, W.; Xiong, F.; Liu, Q.; Xu, L.; Wu, Y.; Chen, F. Substrate Stereocontrol in Bromine-Induced Intermolecular Cyclization: Asymmetric Synthesis of Pitavastatin Calcium. Tetrahedron 2015, 71, 4730–4737.
   PubMed Web of Science ®Google Scholar
• Thompson, A. S.; Humphrey, G. R.; DeMarco, A. M.; Mathre, D. J.; Grabowski, E. J. J. Direct Conversion of Activated Alcohols to Azides Using Diphenyl Phosphorazidate. A Practical Alternative to Mitsunobu Conditions. J. Org. Chem. 1993, 58, 5886–5888. DOI: 10.1021/jo00074a008.
   Web of Science ®Google Scholar
• Liu, F.; Austin, D. J. A General Synthesis of 5′-Azido-5′-Deoxy-2′,3′-O-Isopropylidene Nucleosides. J. Org. Chem. 2001, 66, 8643–8645. DOI: 10.1021/jo015800m.
   PubMed Web of Science ®Google Scholar
• Yeom, C.-E.; Kim, H. W.; Lee, S. Y.; Kim, B. M. Synlett 2007, 146–150.
   Web of Science ®Google Scholar
• Travis, B. R.; Narayan, R. S.; Borhan, B. Osmium Tetroxide-Promoted Catalytic Oxidative Cleavage of Olefins: An Organometallic Ozonolysis. J. Am. Chem. Soc. 2002, 124, 3824–3825. DOI: 10.1021/ja017295g.
   PubMed Web of Science ®Google Scholar
• We had a problem purchasing methylhydrazine known to be used in the preparation of (1-methylhydrazino)acetate. The synthesis of benzyl (1-methylhydrazino)acetate began with tert-butoxycarbonyl glycine benzyl ester and for the detailed procedure please see in the Supporting Information.
   Google Scholar
• Tanner, D.; Somfai, P. Enantioselective Total Synthesis of (+)-Negamycin. Tetrahedron Lett. 1988, 29, 2373–2376. DOI: 10.1016/S0040-4039(00)86063-3.
   Web of Science ®Google Scholar
• Naidu, S. V.; Kumar, P. A Simple and Efficient Approach to 1,3-Aminoalcohols: Application to the Synthesis of (+)-Negamycin. Tetrahedron Lett. 2007, 48, 3793–3796. DOI: 10.1016/j.tetlet.2007.03.169.
   Web of Science ®Google Scholar