Download PDF
Synlett 2004(10): 1673-1685  
DOI: 10.1055/s-2004-829578
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Physiologically Potent β-Amino Alcohols

Hee-Seung Lee*, Sung Ho Kang*
Center for Molecular Design and Synthesis, Department of Chemistry, School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701, South Korea
Fax: +82(42)8692810; e-Mail: hee-seung_lee@kaist.ac.kr; e-Mail: shkang@kaist.ac.kr;
Further Information

Publication History

Received 29 March 2004
Publication Date:
15 July 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

We have established practical protocols to the stereoselective synthesis of syn- and anti-β-amino alcohols via the electrophile-promoted intramolecular amination of trichloroacetimidates derived from allylic and homoallylic alcohols. Stereoselective total synthesis of natural products containing β-amino alcohol functionality has been achieved by means of these methods.

  • 1 Introduction

  • 2 Mechanistic Considerations

  • 3 Z-Olefinic Allylic Trichloroacetimidates

  • 3.1 Swansonine

  • 3.2 Castanospermine and N-Acetylneuraminic Acid

  • 3.3 Carbapenem

  • 4 Terminal Olefinic Homoallylic Trichloroacetimidates

  • 4.1 Statine and Its Analogues

  • 4.2 Anisomycin and Polyoxamic Acid

  • 4.3 Furanomycin

  • 4.4 Azasugars

  • 5 Z-Olefinic Homoallylic Trichloroacetimidates

  • 6 Miscellaneous Substrates

  • 6.1 Trisubstituted Olefins

  • 6.2 1,1-Disubstituted Olefins

  • 6.3 E-Olefinic Allylic Trichloroacetimidates

  • 7 Summary

Key words

β-amino alcohols - natural products - trichloroacetimidate - electrophile-promoted - intramolecular amination

    References

  • 6-1 Bergmeier SC. Tetrahedron  2000,  56:  2561 
    Google Scholar
  • 6-2 Kempf DJ. Sowin TJ. Doherty EM. Hannick SM. Codavoci L. Henry RF. Green BE. Spanton SG. Norbeck DW. J. Org. Chem.  1992,  57:  5692 
    Google Scholar
  • 6-3 Chan MF. Hsiao CN. Tetrahedron Lett.  1992,  33:  3567 
    Google Scholar
  • 6-4 Baker WR. Condon SL. J. Org. Chem.  1993,  58:  3277 
    Google Scholar
  • 6-5 Elbein AD. FASEB  1991,  5:  3055 
    Google Scholar
  • 6-6 Ager DJ. Prakash I. Schaad DR. Chem. Rev.  1996,  96:  835 
    Google Scholar
  • 6-7 Reetz MT. Chem. Rev.  1999,  99:  1121 
    Google Scholar
  • 6-8 Paleo MR. Calaza MI. Sardina FJ. J. Org. Chem.  1997,  62:  6862 
    Google Scholar
  • 6-9 Sasai H. Itoh N. Suzuki T. Shibasaki M. Tetrahedron Lett.  1993,  34:  7693 
    Google Scholar
  • 6-10 Fisher GB. Goralski CT. Nicholson LW. Hasha DL. Zakett D. Singaram B. J. Org. Chem.  1995,  60:  2026 
    Google Scholar
  • 6-11 Castejon P. Moyano A. Pericas MA. Riera A. Tetrahedron  1996,  52:  7063 
    Google Scholar
  • 6-12 Bongini A. Cardillo G. Orena M. Sandri S. Tomasini C. J. Org. Chem.  1986,  51:  4905 
    Google Scholar
  • For a review see:
  • 6-13a Cardillo G. Orena M. Tetrahedron  1990,  46:  3321 
    Google Scholar
  • 6-13b Orena M. In Houben-Weyl, Methods of Organic Chemistry, Stereoselective Synthesis   Vol. E 21e:  Thieme; Stuttgart: 1996.  p.5291-5355  
    Google Scholar
  • 6-14 Chamberlin AR. Mulholland RL. Kahn SD. Hehre WJ. J. Am. Chem. Soc.  1987,  109:  672 
    Google Scholar
  • 6-15 Elbein AD. Molyneux RJ. Alkaloids: Chemical and Biological Perspectives   Vol. 5:  Pelletier SW. Wiley-Interscience; New York: 1987.  p.1 
    Google Scholar
  • 6-16 Kang SH. Kim GT. Tetrahedron Lett.  1995,  36:  5049 
    Google Scholar
  • 6-17 Kang SH. Kim JS. Youn J.-H. Tetrahedron Lett.  1998,  39:  9047 
    Google Scholar
  • 6-18 Kang SH. Kim JS. Chem. Commun.  1998,  1353 
    Google Scholar
  • 6-19 Kang SH. Choi H.-W. Kim JS. Youn J.-H. Chem. Commun.  2000,  227 
    Google Scholar
  • 6-20 Cha JK. Christ WJ. Kishi Y. Tetrahedron Lett.  1983,  24:  3943 
    Google Scholar
  • 6-21 Shih DH. Baker F. Cama L. Christensen BG. Heterocycles  1984,  21:  29 
    Google Scholar
  • 6-22 Kang SH. Kim M. Ryu DH. Synlett  2003,  1149 
    Google Scholar
  • 6-23 Kaga H. Kobayashi S. Ohno M. Tetrahedron Lett.  1989,  30:  113 
    Google Scholar
  • 6-24 Kang SH. Ryu DH. Bull. Korean Chem. Soc.  1996,  17:  219 
    Google Scholar
  • 6-25 Umezawa H. Aoyagi T. Morishima H. Matsuzaki M. Hamada M. Takeuchi T. J. Antibiot.  1970,  23:  259 
    Google Scholar
  • 6-26 Kang SH. Ryu DH. Bioorg. Med. Chem. Lett.  1995,  5:  2959 
    Google Scholar
  • 6-27 Nebois P. Greene AE. J. Org. Chem.  1996,  61:  5210 
    Google Scholar
  • 6-28 Rich DH. Moon BJ. Boparai AS. J. Org. Chem.  1980,  45:  2288 
    Google Scholar
  • 6-29 Iizuka K. Kamijo T. Kubota T. Akahane K. Umeyama H. Kiso Y. J. Med. Chem.  1988,  31:  701 
    Google Scholar
  • 6-30 Pasto M. Castejon P. Moyano A. Pericas MA. Riera A. J. Org. Chem.  1996,  61:  6033 
    Google Scholar
  • 6-31 Suda H. Takita T. Aoyagi T. Uemezawa H. J. Antibiot.  1976,  29:  100 
    Google Scholar
  • 6-32 Righi G. D’Achille C. Pescatore G. Bonini C. Tetrahedron Lett.  2003,  44:  6999 
    Google Scholar
  • 6-33 Grollman AP. Walsh M. J. Biol. Chem.  1967,  242:  3226 
    Google Scholar
  • 6-34 Schwardt O. Veith U. Gaspard C. Jager V. Synthesis  1999,  1473 
    Google Scholar
  • 6-35 Savage I. Thomas EJ. J. Chem. Soc., Chem. Commun.  1989,  717 
    Google Scholar
  • 6-36 Kang SH. Choi H.-w. Chem. Commun.  1996,  1521 
    Google Scholar
  • 6-37 Katagiri K. Tori K. Kimura Y. Yoshida T. Nagasaki T. Minato H. J. Med. Chem.  1967,  10:  1149 
    Google Scholar
  • 6-38 Kohno T. Kohda D. Haruki M. Yokoyama S. Miyazawa T. J. Biol. Chem.  1990,  265:  6931 
    Google Scholar
  • 6-39 Parry RJ. Buu HP. J. Am. Chem. Soc.  1983,  105:  7446 
    Google Scholar
  • 6-40 Parry RJ. Turakhia R. Buu Hanh P. J. Am. Chem. Soc.  1988,  110:  4035 
    Google Scholar
  • 6-41 Kang SH. Lee SB. Chem. Commun.  1998,  761 
    Google Scholar
  • 6-42 Kang SH. Ryu DH. Chem. Commun.  1996,  355 
    Google Scholar
  • 6-43 Kang SH. Ryu DH. Tetrahedron Lett.  1997,  38:  607 
    Google Scholar
  • 6-44 Kang SH. Hwang YS. Youn JH. Tetrahedron Lett.  2001,  42:  7599 
    Google Scholar
  • 6-45 Kang SH. Hwang YS. Lee HS. Bull. Korean Chem. Soc.  2002,  23:  1195 
    Google Scholar
  • 6-46 Kang SH. Kim GT. Yoo YS. Tetrahedron Lett.  1997,  38:  603 
    Google Scholar
  • 6-47 Omura S. Fujimoto T. Otoguro K. Matsuzaki K. Moriguchi R. Tanaka H. Sasaki Y. J. Antibiot.  1991,  44:  113 
    Google Scholar
  • 6-48 Kang SH. Jun H.-S. Youn J.-H. Synlett  1998,  1045 
    Google Scholar
  • 6-49 Roush WR. Ando K. Powers DB. Palkowitz AD. Halterman RL. J. Am. Chem. Soc.  1990,  112:  6339 
    Google Scholar
  • 6-50 Uno H. Baldwin JE. Russell AT. J. Am. Chem. Soc.  1994,  116:  2139 
    Google Scholar
  • 6-51 Kang SH. Kim CM. Youn J.-H. Tetrahedron Lett.  1999,  40:  3581 
    Google Scholar
  • 6-52 Kingston DGI. Chaudhary AG. Gunatilaka AAL. Middleton ML. Tetrahedron Lett.  1994,  35:  4483 
    Google Scholar