Catalyst recognition of cis-1,2-diols enables site-selective functionalization of complex molecules (original) (raw)

References

1. Mahatthananchai, J., Dumas, A. M. & Bode, J. W. Catalytic selective synthesis. Angew. Chem. Int. Ed. 51, 10954–10990 (2012).
   CAS Google Scholar
2. Butler, M. S. Natural products to drugs: natural product-derived compounds in clinical trials. Nat. Prod. Rep. 25, 475–516 (2008).
   CAS PubMed Google Scholar
3. van Kooyk, Y. & Rabinovich, G. A. Protein–glycan interactions in the control of innate and adaptive immune responses. Nature Immunol. 9, 593–601 (2008).
   CAS Google Scholar
4. Helenius, A. & Aebi, M. Intracellular functions of N-linked glycans. Science 291, 2364–2369 (2001).
   CAS PubMed Google Scholar
5. Weymouth-Wilson, A. C. The role of carbohydrates in biologically active natural products. Nat. Prod. Rep. 14, 99–110 (1997).
   CAS PubMed Google Scholar
6. La Ferla, B. et al. Natural glycoconjugates with antitumor activity. Nat. Prod. Rep. 28, 630–648 (2011).
   CAS PubMed Google Scholar
7. Seeberger, P. H. & Werz, D. B. Automated synthesis of oligosaccharides as a basis for drug discovery. Nature Rev. Drug. Discov. 4, 751–763 (2005).
   CAS Google Scholar
8. Zhu, X. & Schmidt, R. R. New principles for glycoside-bond formation. Angew. Chem. Int. Ed. 48, 1900–1934 (2009).
   CAS Google Scholar
9. Hsu, C. H., Hung, S. C., Wu, C. Y. & Wong, C. H. Toward automated oligosaccharide synthesis. Angew. Chem. Int. Ed. 50, 11872–11923 (2011).
   CAS Google Scholar
10. Walczak, M. A. & Danishefsky, S. J. Solving the convergence problem in the synthesis of triantennary _N_-glycan relevant to prostate-specific membrane antigen (PSMA). J. Am. Chem. Soc. 134, 16430–16433 (2012).
    CAS PubMed PubMed Central Google Scholar
11. Breslow, R. et al. Remote oxidation of steroids by photolysis of attached benzophenone groups. J. Am. Chem. Soc. 95, 3251–3262 (1973).
    CAS PubMed Google Scholar
12. Breslow, R. et al. Selective halogenation of steroids using attached aryl iodide templates. J. Am. Chem. Soc. 99, 905–915 (1977).
    CAS PubMed Google Scholar
13. Breslow, R. & Heyer, D. Catalytic multiple template-directed steroid chlorinations. J. Am. Chem. Soc. 104, 2045–2046 (1982).
    CAS Google Scholar
14. Lewis, C. A. & Miller, S. J. Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts. Angew. Chem. Int. Ed. 45, 5616–5619 (2006).
    CAS Google Scholar
15. Chen, M. S. & White, M. C. A predictably selective aliphatic C–H oxidation reaction for complex molecule synthesis. Science 318, 783–787 (2007).
    CAS PubMed Google Scholar
16. Yoshida, K., Furuta, T. & Kawabata, T. Perfectly regioselective acylation of a cardiac glycoside, digitoxin, via catalytic amplification of the intrinsic reactivity. Tetrahedron Lett. 51, 4830–4832 (2010).
    CAS Google Scholar
17. Snyder, S. A., Gollner, A. & Chiriac, M. I. Regioselective reactions for programmable resveratrol oligomer synthesis. Nature 474, 461–466 (2011).
    CAS PubMed PubMed Central Google Scholar
18. Bruckl, T., Baxter, R. D., Ishihara, Y. & Baran, P. S. Innate and guided C–H functionalization logic. Acc. Chem. Res. 45, 826–839 (2012).
    CAS PubMed Google Scholar
19. Pathak, T. P. & Miller, S. J. Site-selective bromination of vancomycin. J. Am. Chem. Soc. 134, 6120–6123 (2012).
    CAS PubMed PubMed Central Google Scholar
20. Wilcock, B. C. et al. Electronic tuning of site-selectivity. Nature Chem. 4, 996–1003 (2012).
    CAS Google Scholar
21. Fowler, B. S., Laemmerhold, K. M. & Miller, S. J. Catalytic site-selective thiocarbonylations and deoxygenations of vancomycin reveal hydroxyl-dependent conformational effects. J. Am. Chem. Soc. 134, 9755–9761 (2012).
    CAS PubMed PubMed Central Google Scholar
22. Beale, T. M. & Taylor, M. S. Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin. Org. Lett. 15, 1358–1361 (2013).
    CAS PubMed Google Scholar
23. Pathak, T. P. & Miller, S. J. Chemical tailoring of teicoplanin with site-selective reactions. J. Am. Chem. Soc. 135, 8415–8422 (2013).
    CAS PubMed PubMed Central Google Scholar
24. Lee, D. & Taylor, M. S. Catalyst-controlled regioselective reactions of carbohydrate derivatives. Synthesis 44, 3421–3431 (2012).
    CAS Google Scholar
25. Kawabata, T., Muramatsu, W., Nishio, T., Shibata, T. & Schedel, H. A catalytic one-step process for the chemo- and regioselective acylation of monosaccharides. J. Am. Chem. Soc. 129, 12890–12895 (2007).
    CAS PubMed Google Scholar
26. Kawabata, T. & Furuta, T. Nonenzymatic regioselective acylation of carbohydrates. Chem. Lett. 38, 640–647 (2009).
    CAS Google Scholar
27. Griswold, K. S. & Miller, S. J. A peptide-based catalyst approach to regioselective functionalization of carbohydrates. Tetrahedron 59, 8869–8875 (2003).
    CAS Google Scholar
28. Gouliaras, C., Lee, D., Chan, L. & Taylor, M. S. Regioselective activation of glycosyl acceptors by a diarylborinic acid-derived catalyst. J. Am. Chem. Soc. 133, 13926–13929 (2011).
    CAS PubMed Google Scholar
29. Chan, L. & Taylor, M. S. Regioselective alkylation of carbohydrate derivatives catalyzed by a diarylborinic acid derivative. Org. Lett. 13, 3090–3093 (2011).
    CAS PubMed Google Scholar
30. Lee, D. & Taylor, M. S. Borinic acid-catalyzed regioselective acylation of carbohydrate derivatives. J. Am. Chem. Soc. 133, 3724–3727 (2011).
    CAS PubMed Google Scholar
31. Lee, D., Williamson, C. L., Chan, L. & Taylor, M. S. Regioselective, borinic acid-catalyzed monoacylation, sulfonylation and alkylation of diols and carbohydrates: expansion of substrate scope and mechanistic studies. J. Am. Chem. Soc. 134, 8260–8267 (2012).
    CAS PubMed Google Scholar
32. Hu, G. & Vasella, A. Regioselective benzoylation of 6-O-protected and 4,6-O-diprotected hexopyranosides as promoted by chiral and achiral ditertiary 1,2-diamines. Helv. Chim. Acta 85, 4369–4391 (2002).
    CAS Google Scholar
33. Page, M. I. & Jencks, W. P. Entropic contributions to rate accelerations in enzymic and intramolecular reactions and chelate effect. Proc. Natl Acad. Sci. USA 68, 1678–1683 (1971).
    CAS PubMed PubMed Central Google Scholar
34. Lobsanov, Y. D. et al. Structure of Kre2p/Mnt1p: a yeast α 1,2-mannosyltransferase involved in mannoprotein biosynthesis. J. Biol. Chem. 279, 17921–17931 (2004).
    CAS PubMed Google Scholar
35. Sun, X., Worthy, A. D. & Tan, K. L. Scaffolding catalysts: highly enantioselective desymmetrization reactions. Angew. Chem. Int. Ed. 50, 8167–8171 (2011).
    CAS Google Scholar
36. Worthy, A. D., Sun, X. & Tan, K. L. Site-selective catalysis: toward a regiodivergent resolution of 1,2-diols. J. Am. Chem. Soc. 134, 7321–7324 (2012).
    CAS PubMed PubMed Central Google Scholar
37. Zhao, Y., Rodrigo, J., Hoveyda, A. H. & Snapper, M. L. Enantioselective silyl protection of alcohols catalysed by an amino-acid-based small molecule. Nature 443, 67–70 (2006).
    CAS PubMed Google Scholar
38. Isobe, T., Fukuda, K., Araki, Y. & Ishikawa, T. Modified guanidines as chiral superbases: the first example of asymmetric silylation of secondary alcohols. Chem. Commun. 7, 243–244 (2001).
    Google Scholar
39. Weickgenannt, A., Mewald, M. & Oestreich, M. Asymmetric Si–O coupling of alcohols. Org. Biomol. Chem. 8, 1497–1504 (2010).
    CAS PubMed Google Scholar
40. Zhao, Y., Mitra, A. W., Hoveyda, A. H. & Snapper, M. L. Kinetic resolution of 1,2-diols through highly site- and enantioselective catalytic silylation. Angew. Chem. Int. Ed. 46, 8471–8474 (2007).
    CAS Google Scholar
41. Rodrigo, J. M., Zhao, Y., Hoveyda, A. H. & Snapper, M. L. Regiodivergent reactions through catalytic enantioselective silylation of chiral diols. Synthesis of sapinofuranone A. Org. Lett. 13, 3778–3781 (2011).
    CAS PubMed PubMed Central Google Scholar
42. Sheppard, C. I., Taylor, J. L. & Wiskur, S. L. Silylation-based kinetic resolution of monofunctional secondary alcohols. Org. Lett. 13, 3794–3797 (2011).
    CAS PubMed Google Scholar
43. Weickgenannt, A., Mohr, J. & Oestreich, M. Catalytic enantioselective dehydrogenative Si–O coupling of oxime ether-functionalized alcohols. Tetrahedron 68, 3468–3479 (2012).
    CAS Google Scholar
44. Pascal, R. Catalysis through induced intramolecularity: what can be learned by mimicking enzymes with carbonyl compounds that covalently bind substrates? Eur. J. Org. Chem., 10, 1813–1824 (2003).
    Google Scholar
45. Tan, K. L. Induced intramolecularity: an effective strategy in catalysis. ACS Cat. 1, 877–886 (2011).
    CAS Google Scholar
46. Guimond, N., MacDonald, M. J., Lemieux, V. & Beauchemin, A. M. Catalysis through temporary intramolecularity: mechanistic investigations on aldehyde-catalyzed Cope-type hydroamination lead to the discovery of a more efficient tethering catalyst. J. Am. Chem. Soc. 134, 16571–16577 (2012).
    CAS PubMed Google Scholar
47. MacDonald, M. J., Hesp, C. R., Schipper, D. J., Pesant, M. & Beauchemin, A. M. Highly enantioselective intermolecular hydroamination of allylic amines with chiral aldehydes as tethering catalysts. Chem. Eur. J. 19, 2597–2601 (2013).
    CAS PubMed Google Scholar
48. Somoza, A. Protecting groups for RNA synthesis: an increasing need for selective preparative methods. Chem. Soc. Rev. 37, 2668–2675 (2008).
    CAS PubMed Google Scholar
49. Repke, K. R. H. & Megges, R. Status and prospect of current inotropic agents. Expert Opin. Ther. Pat. 7, 1297–1306 (1997).
    CAS Google Scholar
50. Thomas, C. M., Hothersall, J., Willis, C. L. & Simpson, T. J. Resistance to and synthesis of the antibiotic mupirocin. Nature Rev. Microbiol. 8, 281–289 (2010).
    CAS Google Scholar
51. Silvian, L. F., Wang, J. & Steitz, T. A. Insights into editing from an Ile-tRNA synthetase structure with tRNA(Ile) and mupirocin. Science 285, 1074–1077 (1999).
    CAS PubMed Google Scholar

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