Download PDF
Synlett 2010(11): 1685-1687  
DOI: 10.1055/s-0029-1219961
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Botryllamides and Lansiumamides via Ruthenium-Catalyzed Hydroamidation of Alkynes

Lukas J. Gooßen*, Mathieu Blanchot, Matthias Arndt, Kifah S. M. Salih
Institut für Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Str., Building 54, 67663 Kaiserslautern, Germany
Fax: +49(631)2053921; e-Mail: goossen@chemie.uni-kl.de;
Further Information

Publication History

Received 26 March 2010
Publication Date:
04 June 2010 (online)

   Permissions and Reprints All articles of this category
Preview

Abstract

Ruthenium-catalyzed hydroamidations of alkynes allow a concise synthetic entry to both E- and Z-configured enamide natural products. This was demonstrated by the synthesis of botryllamides C and E, lansiumamides A and B, and lansamide I in 1-3 steps and 57-98% yield from simple, commercially available precursors.

Key words

alkyne - botryllamide - hydroamidation - lansamide - lansiumamide - ruthenium

    References and Notes

  • 1a Kohno J. Koguchi Y. Nishio M. Nakao K. Kuroda M. Shimizu R. Ohnuki T. Komatsubara S. J. Org. Chem.  2000,  65:  990 
    Search in Google Scholar
  • 1b Kunze B. Jansen R. Höfle G. Reichenbach H. J. Antibiot.  1994,  47:  881 
    Search in Google Scholar
  • 1c Ghosh S. Datta DB. Sen N. Synth. Commun.  1987,  17:  299 
    Search in Google Scholar
  • 1d Maxwell A. Rampersad D. J. Nat. Prod.  1989,  52:  411 
    Search in Google Scholar
  • 1e Estévez JC. Villaverde MC. Estévez RJ. Seijas JA. Castedo L. Synth. Commun.  1990,  20:  503 
    Search in Google Scholar
  • 2 Toske SG. Jensen PR. Kaufman CA. Fenical W. Tetrahedron  1998,  54:  13459 
    CrossrefSearch in Google Scholar
  • 3 Han YN. Kim G.-Y. Han HK. Han BH. Arch. Pharmacol. Res.  1993,  16:  289 
    CrossrefSearch in Google Scholar
  • 4 Yet L. Chem. Rev.  2003,  103:  4283 
    CrossrefPubMedSearch in Google Scholar
  • 5a Dupau P. Le Gendre P. Bruneau C. Dixneuf PH. Synlett  1999,  1832 
  • 5b Wang X. Porco JA. J. Org. Chem.  2001,  66:  8215 
    Search in Google Scholar
  • 5c Bayer A. Maier ME. Tetrahedron  2004,  60:  6665 
    Search in Google Scholar
  • 5d Boeckman RK. Goldstein SW. Walters MA. J. Am. Chem. Soc.  1988,  110:  8250 
    Search in Google Scholar
  • 5e Kinderman SS. van Maarseveen JH. Schoemaker HE. Hiemstra H. Rutjes FPJT. Org. Lett.  2001,  3:  2045 
    Search in Google Scholar
  • 6a Pa X. Cai Q. Ma D. Org. Lett.  2004,  6:  1809 
    Search in Google Scholar
  • 6b Wallace J. Klauber DJ. Chen C. Volante RP. Org. Lett.  2003,  5:  4749 
    Search in Google Scholar
  • 6c Brice JL. Meerdink JE. Stahl S. Org. Lett.  2004,  6:  1845 
    Search in Google Scholar
  • 7 Kondo T. Tanaka A. Kotachi S. Watanabe Y. J. Chem. Soc., Chem. Commun.  1995,  413 
    Crossref
  • For addition reactions of other hydrogen-bonded nucleophiles to alkynes, see:
  • 8a Mitsudo T.-A. Hori Y. Watanabe Y. J. Org. Chem.  1985,  50:  1566 
    Search in Google Scholar
  • 8b Doucet H. Derrien N. Kabouche Z. Bruneau C. Dixneuf PH. J. Organomet. Chem.  1997,  551:  151 
    Search in Google Scholar
  • 8c Gooßen LJ. Paetzold J. Koley D. Chem. Commun.  2003,  706 
  • 8d Pholki F. Doye S. Chem. Soc. Rev.  2003,  32:  104 
    Search in Google Scholar
  • 8e Beller M. Seayad J. Tillack A. Jiao H. Angew. Chem. Int. Ed.  2004,  43:  3368 ; Angew. Chem. 2004, 116, 3448
    Search in Google Scholar
  • 8f Tokunaga M. Suzuki T. Koga N. Fukushima T. Horiuchi A. Wakatsuki Y. J. Am. Chem. Soc.  2001,  123:  11917 
    Search in Google Scholar
  • 8g Hashmi ASK. Hutchings GJ. Angew. Chem. Int. Ed.  2006,  45:  7896 ; Angew. Chem. 2006, 118, 8064
    Search in Google Scholar
  • For recent reviews, see:
  • 9a Alonso F. Beletskaya IP. Yus M. Chem. Rev.  2004,  104:  3079 
    Search in Google Scholar
  • 9b Bruneau C. Dixneuf PH. Angew. Chem. Int. Ed.  2006,  45:  2176 ; Angew. Chem. 2006, 118, 2232
    Search in Google Scholar
  • 10a Gooßen LJ. Rauhaus JE. Deng G. Angew. Chem. Int. Ed.  2005,  44:  4042 ; Angew. Chem. 2005, 117, 4110
    Search in Google Scholar
  • 10b Gooßen LJ. Blanchot M. Brinkmann C. Gooßen K. Karch R. Rivas-Nass A. J. Org. Chem.  2006,  71:  9506 
    Search in Google Scholar
  • 10c Gooßen LJ. Salih KSM. Blanchot M. Angew. Chem. Int. Ed.  2008,  47:  8492 ; Angew. Chem. 2008, 120, 8620
    Search in Google Scholar
  • 10d Gooßen LJ. Arndt M. Blanchot M. Rudolphi F. Menges F. Niedner-Schatteburg G. Adv. Synth. Catal.  2008,  350:  2701 
    Search in Google Scholar
  • 10e Gooßen LJ. Blanchot M. Salih KSM. Gooßen K. Synthesis  2009,  2283 
  • 10f Gooßen LJ. Blanchot M. Salih KSM. Karch R. Rivas-Nass A. Org. Lett.  2008,  10:  4497 
    Search in Google Scholar
  • Isolation:
  • 11a Lin J.-H. Phytochemistry  1989,  28:  621 ; and references cited therein
    Search in Google Scholar
  • Synthesis:
  • 11b Stefanuti I. Smith SA. Taylor RJK. Tetrahedron Lett.  2000,  41:  3735 
    Search in Google Scholar
  • 11c Fürstner A. Brehm C. Cancho-Grande Y. Org. Lett.  2001,  3:  3955 
    Search in Google Scholar
  • 11d Bayer A. Maier ME. Tetrahedron  2004,  60:  6665 
    Search in Google Scholar
  • 12a Rao MR. Faulkner DJ. J. Nat. Prod.  2004,  67:  1064 
    Search in Google Scholar
  • 12b McKay MJ. Carroll AR. Quinn RJ. J. Nat. Prod.  2005,  68:  1776 
    Search in Google Scholar
  • 12c Henrich CJ. Robey RW. Takada K. Bokesch HR. Bates SE. Shukla S. Ambudkar SV. McMahon JB. Gustafson KR. ACS Chem. Biol.  2009,  4:  637 
    Search in Google Scholar
  • 12d Takada K. Imamura N. Gustafson KR. Henrich CJ. Bioorg. Med. Chem. Lett.  2010,  20:  1330 
    Search in Google Scholar
  • 12e McDonald LA. Swersey JC. Ireland CM. Tetrahedron  1995,  51:  5237 
    Search in Google Scholar
  • 15a Ohira S. Synth. Commun.  1989,  19:  561 
    Search in Google Scholar
  • 15b Müller S. Liepold B. Roth GJ. Bestmann HJ. Synlett  1996,  521 
  • 15c Roth GJ. Liepold B. Müller SG. Bestmann HJ. Synthesis  2004,  59 
  • 15d For the synthesis of the Bestmann-Ohira reagent 14, see: Pietruszka J. Witt A. Synthesis  2006,  4266 
13

CCDC 768748 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

14

CCDC 768747 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.