Synthesis 2012(3): 409-416  
DOI: 10.1055/s-0031-1289656
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Approaches to Highly Functional β-Carboline Building Blocks via Allylic Amidation

Johannes F. Teichert, Martín Fañanás-Mastral, Ben L. Feringa*
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands
Fax: +31(50)3634296; e-Mail: b.l.feringa@rug.nl;
Further Information

Publication History

Received 7 November 2011
Publication Date:
22 December 2011 (eFirst)

Abstract

A new, straightforward synthesis of highly functional β-carboline building blocks is presented that makes use of allylic amidation methodology. The products obtained carry a terminal double bond as well as an easy-to-deprotect amide, which make them perfectly suitable for further functionalization. The use of the trifluoroacetamide group is exploited in a dual fashion; it acts as a protecting group and functions as the nucleophile for the allylic amidation reaction.

    References

  • 1 Cao RH. Peng WL. Wang ZH. Xu AL. Curr. Med. Chem.  2007,  14:  479 
  • 2 Dewick PM. Medicinal Natural Products - A Biosynthetic Approach   2nd ed.:  Wiley; Chichester: 2001. 
  • 3 Somei M. Yamada F. Nat. Prod. Rep.  2005,  22:  73 
  • 4 Kochanowska-Karamyan AJ. Hamann MT. Chem. Rev.  2010,  110:  4489 
  • 5 Prevatt-Smith KM. Prisinzano TE. Nat. Prod. Rep.  2010,  27:  23 
  • 6 Aygun A. Pindur U. Curr. Med. Chem.  2003,  10:  1113 
  • 7 Shamon SD. Perez MI. Cochrane Database Syst. Rev.  2009,  (4):  CD007655 
  • 8 Chen FE. Huang J. Chem. Rev.  2005,  105:  4671 
  • 9 Lewis SE. Tetrahedron  2006,  62:  8655 
  • 10 Bandini M. Eichholzer A. Angew. Chem. Int. Ed.  2009,  48:  9608 
  • 11 Borschberg HR. Curr. Org. Chem.  2005,  9:  1465 
  • 12 Scholz U. Winterfeldt E. Nat. Prod. Rep.  2000,  17:  349 
  • 13 Marques-Lopez E. Diez-Martinez A. Merino P. Herrera RP. Curr. Org. Chem.  2009,  13:  1585 
  • 14 Martin SF. Acc. Chem. Res.  2002,  35:  895 
  • 15 Padwa A. Heidelbaugh TM. Kuethe JT. McClure MS. Wang Q. J. Org. Chem.  2002,  67:  5928 
  • 16 Teichert JF. Fañanás-Mastral M. Feringa BL. Angew. Chem. Int. Ed.  2011,  50:  688 
  • 17 Helmchen G. Dahnz A. Dübon P. Schelwies M. Weihofen R. Chem. Commun.  2007,  675 
  • 18 Bartels B. Garcia-Yebra C. Helmchen G. Eur. J. Org. Chem.  2003,  1097 
  • 19 Spiess S. Welter C. Franck G. Taquet JP. Helmchen G. Angew. Chem. Int. Ed.  2008,  47:  7652 
  • 20 Kiener CA. Shu CT. Incarvito C. Hartwig JF. J. Am. Chem. Soc.  2003,  125:  14272 
  • 21 Ohmura T. Hartwig JF. J. Am. Chem. Soc.  2002,  124:  15164 
  • 22 Marković D. Hartwig JF. J. Am. Chem. Soc.  2007,  129:  11680 
  • 23 Teichert JF. Feringa BL. Angew. Chem. Int. Ed.  2010,  49:  2486 
  • 24 Mingoia Q. Gazz. Chim. Ital.  1930,  60:  509 
  • 26 Betzer JF. Delaloge F. Muller B. Pancrazi A. Prunet J. J. Org. Chem.  1997,  62:  7768 
  • 27 Shi C. Ojima I. Tetrahedron  2007,  63:  8563 
25

N-Benzyltryptamine 7b could also be trapped with acrolein after lithiation to give secondary allylic alcohol 12 (Scheme 6). See the experimental section for details.

Scheme 6