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Synthesis 2009(17): 2954-2962  
DOI: 10.1055/s-0029-1216910
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereochemical Assignments of the Chlorinated Residues in Victorin C

Amanda C. Durow, Craig Butts, Christine L. Willis*
School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, UK
Fax: +44(117)0298611; e-Mail: chris.willis@bristol.ac.uk;
Further Information

Publication History

Received 30 May 2009
Publication Date:
23 July 2009 (online)

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Abstract

Victorins are cyclic pentapeptide natural products isolated from the fungus Cochliobus victoriae. Using a combination of synthesis and spectroscopic methods we have assigned the geometry of the vinyl chloride residue and determined the stereochemistry of the 5,5-dichloroleucine moiety.

Key words

amino acids - halogenation - natural products - spectroscopy - stereoselective synthesis

    References

  • 1a Macko V. Wolpert TJ. Acklin W. Jaun B. Seibl J. Meili J. Arigoni D. Experientia  1985,  41:  1366 
    Google Scholar
  • 1b Wolpert TJ. Macko V. Acklin W. Jaun B. Seibl J. Meili J. Arigoni D. Experientia  1985,  41:  1524 
    Google Scholar
  • 1c Wolpert TJ. Macko V. Acklin W. Jaun B. Arigoni D. Experientia  1986,  42:  1296 
    Google Scholar
  • 1d Gloer JB. Meinwald J. Walton JD. Earle ED. Experientia  1985,  41:  1370 
    Google Scholar
  • 2a Kono Y. Kinoshita T. Takeuchi S. Daly JM. Agric. Biol. Chem.  1986,  50:  2689 
    Google Scholar
  • 2b Kono Y. Kinoshita T. Takeuchi S. Daly JM. Agric. Biol. Chem.  1989,  53:  505 
    Google Scholar
  • 2c Kinoshita T. Kono Y. Takeuchi S. Daly JM. Agric. Biol. Chem.  1989,  53:  1283 
    Google Scholar
  • 3 Leibold T. Sasse F. Reichenbach H. Höfle G. Eur. J. Org. Chem.  2004,  431 
    CrossrefGoogle Scholar
  • See for example:
  • 4a Brown AG. Smale TC. Chem. Commun.  1969,  1489 
    Google Scholar
  • 4b Srinivasan A. Richards KD. Olsen RK. Tetrahedron Lett.  1976,  17:  891 
    Google Scholar
  • 4c Morgenstern P. Schutij C. Nauta WT. Chem. Commun.  1969,  321 
    Google Scholar
  • 4d Graham DW. Ashton WT. Barash L. Brown JE. Brown RD. Canning LF. Chen A. Springer JP. Rogers EF. J. Med. Chem.  1987,  30:  1074 
    Google Scholar
  • 5 Labia R. Morin C. J. Org. Chem.  1986,  51:  249 
    CrossrefGoogle Scholar
  • 6 Kolar AJ. Olsen RK. J. Org. Chem.  1980,  45:  3246 
    CrossrefGoogle Scholar
  • 7a Marshall JL. Methods in Stereochemical Analysis, Vol. 2   VCH; Weinheim: 1983. 
    Google Scholar
  • 7b Fischer P. Schweizer E. Langer J. Schmidt U. Magn. Reson. Chem.  1994,  32:  567 
    Google Scholar
  • See for example:
  • 8a Sitachitta N. Marquez BL. Williamson RT. Rossi J. Roberts MA. Nguyen V.-A. Willis CL. Tetrahedron  2000,  56:  9103 
    Google Scholar
  • 8b Su J.-Y. Zhong Y.-L. Zheng L.-M. Wei S. Wong Q.-W. Mak TCW. Zhou Z.-Y. J. Nat. Prod.  1993,  56:  637 
    Google Scholar
  • 8c Unson MD. Rose CB. Fulkner DJ. Brinen LS. Steiner JR. Clardy J. J. Org. Chem.  1993,  58:  6336 
    Google Scholar
  • 9a Ardá A. Jiménez C. Rodríguez J. Tetrahedron Lett.  2004,  45:  3241 
    Google Scholar
  • 9b Ardá A. Soengas RG. Nieto MI. Jiménez C. Rodríguez J. Org. Lett.  2008,  10:  2175 
    Google Scholar
  • 10 Durow AC. Long GC. O’Connell SJ. Willis CL. Org. Lett.  2006,  8:  5401 
    CrossrefGoogle Scholar
  • 11 Glimie IJG. Evans DA. Tetrahedron  1982,  38:  698 
    Google Scholar
  • 12 Ardá A. Jiménez C. Rodríguez J. Eur. J. Org. Chem.  2006,  3645 
    CrossrefGoogle Scholar
  • 13 Takeda T. Sasaki R. Yamaguchi S. Fujiwara T. Tetrahedron  1997,  53:  557 
    CrossrefGoogle Scholar
  • 14 Charrier J.-D. Duffy JES. Hitchcock PB. Young DW. J. Chem. Soc., Perkin Trans. 1  2001,  2367 
    CrossrefGoogle Scholar
  • 15 Tarver JE. Terranova KM. Joullié MM. Tetrahedron  2004,  60:  10277 
    CrossrefGoogle Scholar
  • 16 Charrier J.-D. Hadfield DS. Hitchcock PB. Young DW. Org. Biomol. Chem.  2004,  2:  474 
    CrossrefGoogle Scholar
  • 17 Gigg R. Gigg J. J. Chem. Soc.  1968,  15:  1651 
    Google Scholar
  • 18 Dess DB. Martin JC. J. Am. Chem. Soc.  1991,  113:  7277 
    CrossrefGoogle Scholar
  • 20 Richards KD. Kolar A. Srinivasan A. Stephenson RW. Olsen RK. J. Org. Chem.  1976,  41:  3674 
    CrossrefGoogle Scholar
19

The optical rotation has not been reported for 5,5-dichloroleucine isolated following degradation of the victorins,¹,² hence the absolute stereochemistry is assumed from the earlier reported ORD shifts of the 2,4-DNP derivatives.²