공업화학 (Applied Chemistry for Engineering)

  • 제25권5호
  • /
  • Pages.437-446
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  • 2014
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  • 1225-0112(pISSN)
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  • 2288-4505(eISSN)
한국공업화학회 (The Korean Society of Industrial and Engineering Chemistry)
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비고리 알릴아민 화합물의 입체선택적 이중알코올화 반응

Stereocontrolled Dihydroxylation Reactions of Acyclic Allylic Amines

  • 전종호 (한국원자력연구원 첨단방사선연구소 생명공학연구부) ;
  • 신나라 (서울대학교 공과대학 화학생물공학부) ;
  • 김영규 (서울대학교 공과대학 화학생물공학부)
  • Jeon, Jongho (Research Division for Biotechnology, Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute) ;
  • Shin, Nara (Department of Chemical and Biological Engineering, Seoul National University) ;
  • Kim, Young Gyu (Department of Chemical and Biological Engineering, Seoul National University)
  • 투고 : 2014.09.30
  • 발행 : 2014.10.10
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초록

비고리 알릴아민 화합물의 이중알코올화 반응은 아미노 다이올 구조를 도입할 수 있는 효율적인 합성법으로 아미노 다이올 구조를 포함하는 다양한 생리활성 천연물의 효율적인 합성에 적용될 수 있다. 본 리뷰에서는 기질 그 자체, 혹은 카이랄 리간드를 이용한 다양한 입체선택적 이중알코올화 반응들을 소개하고 이를 실제 천연물의 합성에 적용한 최근의 반응 결과들을 살펴보고자 한다.

The dihydroxylation reaction of allylic amines is a facile and useful synthetic method to obtain amino diol structures that are widely found in lots of biologically important natural products. This review will focus on the recent methods of both substrate-controlled and ligand-controlled dihydroxylation reactions of acyclic allylic amines. In addition, several applications of the diastereoselective dihydroxylation methods to asymmetric syntheses of natural products are presented.

키워드

참고문헌

  1. S. C. Bergmeier, The synthesis of vicinal amino alcohols, Tetrahedron, 56, 2561 (2000). https://doi.org/10.1016/S0040-4020(00)00149-6
  2. D. J. Ager, I. Prakash, and D. R. Schaad, 1,2-Amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis, Chem. Rev., 96, 835 (1996). https://doi.org/10.1021/cr9500038
  3. J. K. Cha and N.-S. Kim, Acyclic stereocontrol induced by allylic alkoxy groups. Synthetic applications of stereoselective dihydroxylation in natural product synthesis, Chem. Rev., 95, 1761 (1995). https://doi.org/10.1021/cr00038a003
  4. J. K. Cha, W. J. Christ, and Y. Kishi, On stereochemistry of osmium tetroxide oxidation of allylic alcohol systems: Empirical rule, Tetrahedron Lett., 24, 3943 (1983). https://doi.org/10.1016/S0040-4039(00)88231-3
  5. W. J. Christ, J. K. Cha, and Y. Kishi, On stereochemistry of osmium tetroxide oxidation of allylic alcohol systems: Examples, Tetrahedron Lett., 24, 3947 (1983). https://doi.org/10.1016/S0040-4039(00)88232-5
  6. J. K. Cha, W. J. Christ, and Y. Kishi, On stereochemistry of osmium tetraoxide oxidation of allylic alcohol systems. Empirical rule, Tetrahedron, 40, 2247 (1984). https://doi.org/10.1016/0040-4020(84)80008-3
  7. K. N. Houk, H. Y. Duh, Y. D. Wu, and S. R. Moses, Steric models for stereoselectivity of nitrile oxide cycloadditions to chiral alkenes, J. Am. Chem. Soc., 108, 2754 (1986). https://doi.org/10.1021/ja00270a044
  8. E. Vedejs and C. K. McClure, Hyperconjugative effects are not important in osmylations, J. Am. Chem. Soc., 108, 1094 (1986). https://doi.org/10.1021/ja00265a048
  9. T. J. Donohoe, K. Blades, M. Helliwell, P. R. Moore, and J. J. G. Winter, Directed dihydroxylation of allylic trichloroacetamides, J. Org. Chem., 64, 2980 (1999). https://doi.org/10.1021/jo982468e
  10. T. J. Donohoe, K. Blades, P. R. Moore, M. J. Waring, J. J. G. Winter, M. Helliwell, N. J. Newcombe, and G. Stemp, Directed dihydroxylation of cyclic allylic alcohols and trichloroacetamides using $OsO_4$/TMEDA, J. Org. Chem., 67, 7946 (2002). https://doi.org/10.1021/jo026161y
  11. J. A. Olsen, R. Severinsen, T. B. Rasmussen, M. Hentzer, M. Givskov, and J. Nielsen, Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers, Bioorg. Med. Chem. Lett., 12, 325 (2002). https://doi.org/10.1016/S0960-894X(01)00756-9
  12. J. S. Oh, D. Y. Park, B. S. Song, J. G. Bae, S. W. Yoon, and Y. G. Kim, anti Selective dihydroxylation by the ketimine derivatives of the allylic amine in monosubstituted olefins, Tetrahedron Lett., 43, 7209 (2002). https://doi.org/10.1016/S0040-4039(02)01654-4
  13. R. Imashiro, O. Sakurai, T. Yamashita, and H. Horikawa, A short and efficient synthesis of phytosphingosines using asymmetric dihydroxylation, Tetrahedron, 54, 10657 (1998). https://doi.org/10.1016/S0040-4020(98)00615-2
  14. O. Shirota, K. Nakanishi, and N. Berova, Phytosphingosinesa facile synthesis and spectroscopic protocol for configurational assignment, Tetrahedron, 55, 13643 (1999). https://doi.org/10.1016/S0040-4020(99)00839-X
  15. F. Matsuura, Y. Hamada, and T. Shioiri, An efficient synthesis of polyoxamic acid utilizing the aryl group as the carboxyl synthon. A new approach to polyhydroxyamino acids, Tetrahedron Lett., 35, 733 (1994). https://doi.org/10.1016/S0040-4039(00)75803-5
  16. E. C. Shuter, H. Duong, C. A. Hutton, and M. D. McLeod, The enantioselective synthesis of APTO and AETD: polyhydroxylated ${\beta}$-amino acid constituents of the microsclerodermin cyclic peptides, Org. Biomol. Chem., 5, 3183 (2007). https://doi.org/10.1039/b707891a
  17. Q. I. Churches, J. M. White, and C. A. Hutton, Synthesis of ${\beta},{\gamma}$-dihydroxyhomotyrosines by a tandem petasis-Asymmetric dihydroxylation approach, Org. Lett., 13, 2900 (2011). https://doi.org/10.1021/ol200917s
  18. J. Llaveria, Y. Diaz, M. I. Matheu, and S. Castillon, An efficient and general enantioselective synthesis of sphingosine, phythosphingosine, and 4-substituted derivatives, Org. Lett., 11, 205 (2009). https://doi.org/10.1021/ol802379b
  19. N. Hama, T. Aoki, S. Miwa, M. Yamazaki, T. Sato, and N. Chida, Total synthesis of Broussonetine F: The orthoamide Overman rearrangement of an allylic diol, Org. Lett., 13, 616 (2011). https://doi.org/10.1021/ol102856j
  20. K. Csatayova, S. G. Davies, J. A. Lee, P. M. Roberts, A. J. Russell, J. E. Thomson, and D. L. Wilson, Highly diastereoselective and stereodivergent dihydroxylations of acyclic allylic amines: application to the asymmetric synthesis of 3,6-dideoxy-3-amino-L-talose, Org. Lett., 13, 2606 (2011). https://doi.org/10.1021/ol200717n
  21. S. G. Davies, A. M. Fletcher, E. M. Foster, J. A. Lee, P. M. Roberts, and J. E. Thomson, Asymmetric syntheses of APTO and AETD: the ${\beta}$ Amino acid fragments within Microsclerodermins C, D, and E, J. Org. Chem., 78, 2500 (2013). https://doi.org/10.1021/jo302731m
  22. Y. Yoshimitsu, S. Inuki, S. Oishi, N. Fujii, and H. Ohno, Stereoselective divergent synthesis of four diastereomers of pachastrissamine (Jaspine B), J. Org. Chem., 75, 3843 (2010). https://doi.org/10.1021/jo1005284
  23. G. Yang, J. Schmieg, M. Tsuji, and R. W. Franck, The C-glycoside analogue of the immunostimulant ${\alpha}$-galactosylceramide (KRN7000): Synthesis and striking enhancement of activity, Angew. Chem. Int. Ed., 43, 3818 (2004). https://doi.org/10.1002/anie.200454215
  24. K. Csatayova, S. G. Davies, J. G. Ford, J. A. Lee, P. M. Roberts, and James E. Thomson, Asymmetric syntheses of methyl N,O-diacetyl-D-3-epidaunosaminide and methyl N,O-diacetyl-D-ristosaminide, J. Org. Chem., 78, 12397 (2013). https://doi.org/10.1021/jo4020563
  25. J. Jeon, M. Shin, J. W. Yoo, J. S. Oh, J. G. Bae, S. H. Jung, and Y. G. Kim, Highly anti-selective dihydroxylation of 1,2-dialkyl substituted (Z)-allylic amines: Stereoselective synthesis of a D-ribo-phytosphingosine derivative, Tetrahedron Lett., 48, 1105 (2007). https://doi.org/10.1016/j.tetlet.2006.12.084
  26. M. T. Reetz, T. J. Strack, F. Mutulis, and R. Goddard, Asymmetric dihydroxylation of chiral ${\gamma}$-amino-${\alpha},{\beta}$-unsaturated esters: Turning the mismatched into the matched case via protective group tuning, Tetrahedron Lett., 37, 9293 (1996). https://doi.org/10.1016/S0040-4039(97)82945-0
  27. S. D. Broady, J. E. Rexhausen, and E. J. Thomas, Total synthesis of AI-77-B: stereoselective hydroxylation of 4-alkenylazetidinones, J. Chem. Soc., Perkin Trans. 1, 1083 (1999).
  28. J. S. Reddy and B. V. Rao, A sort, efficient, and stereoselective total synthesis of a pyrrolidine alkaloid: (-)-Codonopsinine, J. Org. Chem., 72, 2224 (2007). https://doi.org/10.1021/jo061940q
  29. S. P. Kotkar, V. B. Chavan, and A. Sudalai, Organocatalytic sequential ${\alpha}$-amination-Horner-Wadsworth-Emmons olefination of aldehydes: Enantioselective synthesis of ${\gamma}$-amino-${\alpha},{\beta}$-unsaturated esters, Org. Lett., 9, 1001 (2007). https://doi.org/10.1021/ol063012j
  30. R. Martin, C. Murruzzu, M. A. Pericas, and A. Riera, General approach to glycosidase inhibitors. Enantioselective synthesis of deoxymannojirimycin and swainsonine, J. Org. Chem., 70, 2325 (2005). https://doi.org/10.1021/jo048172s
  31. Y. Huang and D. R. Dalton, The efficient, enantioselective synthesis of aza sugars from amino acids. 1. The polyhydroxylated pyrrolidines, J. Org. Chem., 62, 372 (1997). https://doi.org/10.1021/jo962028s
  32. A. Dondoni, P. Merino, and D. Perrone, Totally chemical synthesis of azasugars via thiazole intermediates. Stereodivergent routes to (-)-nojirimycin, (-)-mannojirimycin and their 3-deoxy derivatives from serine, Tetrahedron, 49, 2939 (1993). https://doi.org/10.1016/S0040-4020(01)80389-6
  33. T. Shinada, E. Ikebe, K. Oe, K. Namba, M. Kawasaki, and Yasufumi Ohfune, Synthesis and absolute structure of manzacidin B, Org. Lett., 9, 1765 (2007). https://doi.org/10.1021/ol0704789
  34. Y. -J. Lee, Y. Park, M. -H. Kim, S. -S. Jew, and H. -G. Park, An enantioselective synthesis of (+)-polyoxamic acid via phase-transfer catalytic conjugate addition and asymmetric dihydroxylation, J. Org. Chem., 76, 740 (2011). https://doi.org/10.1021/jo102272h
  35. K. S. Olivier and M. S. Van Nieuwenhze, Synthetic studies toward the mannopeptimycins: Synthesis of orthogonally protected ${\beta}$-hydroxyenduracididines, Org. Lett., 12, 1680 (2010). https://doi.org/10.1021/ol100219a
  36. A. N. Hulme and C. H. Montgomery, Stereoselective synthesis of the ${\alpha}$-glucosidase inhibitor nectrisine, Tetrahedron Lett., 44, 7649 (2003). https://doi.org/10.1016/j.tetlet.2003.08.030
  37. P. Coutrot, S. Claudel, C. Didierjean, and Claude Grison, Stereoselective synthesis and glycosidase inhibitory activity of 3,4-dihydroxy-pyrrolidin-2-one, 3,4-dihydroxy-piperidin-2-one and 1,2-dihydroxy-pyrrolizidin-3-one, Bioorg. Med. Chem. Lett., 16, 417 (2006). https://doi.org/10.1016/j.bmcl.2005.09.068
  38. J. C. Thoen, A. I. Morales-Ramos, and M. A. Lipton, Synthesis of the unnatural amino acid AGDHE, a constituent of the cyclic depsipeptides callipeltins A and D, Org. Lett., 4, 4455 (2002). https://doi.org/10.1021/ol0269852
  39. J. S. Oh, J. Jeon, D. Y. Park, and Y. G. Kim, Stereoselective dihydroxylation reactions of reactions of ${\gamma}$-amino-${\alpha},{\beta}$-unsaturated esters via their aryl ketimine derivatives, Chem. Commun., 41, 771 (2005).
  40. J. Jeon, S. -K. Hong, J. S. Oh, and Young Gyu Kim, Stereoselective synthesis of protected (2R,3R,4S)-4,7-diamino-2,3-dihydroxyheptanoic acid: A novel amino acid of callipeltins A and D, J. Org. Chem., 71, 3310 (2006). https://doi.org/10.1021/jo052676o
  41. J. Jeon, J. H. Lee, J. -W. Kim, and Y. G. Kim, syn-Selective dihydroxylation of ${\gamma}$-amino-${\alpha},{\beta}$-unsaturated (Z)-esters from D-serine: Stereoselective synthesis of D-iminolyxitol, Tetrahedron: Asymmetry, 18, 2448 (2007). https://doi.org/10.1016/j.tetasy.2007.10.004
  42. J. Jeon, N. Shin, J. H. Lee, and Y. G. Kim, Efficient stereoselective synthesis of (2S,3S,4S)-3,4-dihydroxyglutamic acid, Appl. Chem. Eng., 25, 392 (2014). https://doi.org/10.14478/ace.2014.1045
  43. J. Jeon, S. -H Kim, J. H. Lee, and Y. G. Kim, anti-Selective dihydroxylations of monosubstituted allylic amine and ${\gamma}$-amino-${\alpha},{\beta}$-unsaturated (E)-esters by bulky alkyl groups, Bull. Korean Chem. Soc., 30, 1003 (2009). https://doi.org/10.5012/bkcs.2009.30.5.1003

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