Stereoselective Synthesis of β-Methoxytyrosine Derivatives for Identification of the Absolute Configuration of Callipeltin E

 

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Abstract

Asymmetric syntheses of all diastereoisomers of β-methoxytyrosine, an unusual amino acid contained in callipeltin A, were accomplished starting from a cinnamyl ester derivative. The stereo­chemistry of β-methoxytyrosine in callipeltin E was estimated to be 2R,3R by ¹H and ¹³C NMR analyses of four diastereoisomeric tri­peptides, each containing a β-methoxytyrosine isomer. These results obtained from the synthetic peptide derivatives were identical to D’Auria’s results obtained by a degradative procedure.

References

• 1a Zampella A. D’Auria MV. Gomez-Paloma L. Casapulla A. Debitus C. Henin Y. J. Am. Chem. Soc.  1996,  118:  6202 
  CrossrefGoogle Scholar
• 1b D’Auria MV. Zampella A. Gomez-Paloma L. Minale L. Tetrahedron  1996,  52:  9589 
  CrossrefGoogle Scholar
• 1c Zampella A. Randazzo A. Borbone N. Luciani S. Trevisi L. Debitus C. D’Auria MV. Tetrahedron Lett.  2002,  43:  6163 
  CrossrefGoogle Scholar
• 2a Trevisi L. Bova S. Cargnelli G. Danieli-Betto D. Floreani M. D’Auria MV. Luciani S. Biochem. Biophys. Res. Commun.  2000,  279:  219 
  CrossrefGoogle Scholar
• 2b Trevisi L. Cargnelli G. Ceolotte G. Papparella I. Semplicini A. Zampella A. D’Auria MV. Luciani S. Biochem. Pharmacol.  2004,  68:  1331 
  CrossrefGoogle Scholar
• 3a Liang B. Carroll P. Joullié MM. Org. Lett.  2000,  2:  4157 
  CrossrefGoogle Scholar
• 3b Okamoto N. Hara O. Makino K. Hamada Y. Tetrahedron: Asymmetry  2001,  12:  1353 
  CrossrefGoogle Scholar
• 3c Acevedo CM. Kogut EF. Lipton MA. Tetrahedron  2001,  57:  6353 
  CrossrefGoogle Scholar
• 3d Chandrasekhar S. Ramachandar T. Rao BV. Tetrahedron: Asymmetry  2001,  12:  2315 
  CrossrefGoogle Scholar
• 3e Guerlavais V. Carroll PJ. Joullié MM. Tetrahedron: Asymmetry  2002,  13:  675 
  CrossrefGoogle Scholar
• 3f Zampella A. Sorgente M. D’Auria MV. Tetrahedron: Asymmetry  2002,  13:  681 
  CrossrefGoogle Scholar
• 3g Zampella A. D’Auria MV. Tetrahedron: Asymmetry  2002,  13:  1237 
  CrossrefGoogle Scholar
• 3h Thoen JC. Morales-Ramos AI. Lipton MA. Org. Lett.  2002,  4:  4455 
  CrossrefGoogle Scholar
• 3i Ravi KA. Venkateswara RB. Tetrahedron Lett.  2003,  44:  5645 
  CrossrefGoogle Scholar
• 3j Turk JA. Visbal GS. Lipton MA. J. Org. Chem.  2003,  68:  7841 
  CrossrefGoogle Scholar
• 4 Okamoto N. Hara O. Makino K. Hamada Y. J. Org. Chem.  2002,  67:  9210 
  CrossrefGoogle Scholar
• 5 Hansen DB. Wan X. Carroll PJ. Joullié MM. J. Org. Chem.  2005,  70:  3120 
  CrossrefGoogle Scholar
• 6 Zampella A. D’Orsi R. Sepe V. Casapullo A. Monti MC. D’Auria MV. Org. Lett.  2005,  7:  3585 
  CrossrefGoogle Scholar
• 7 Calimsiz S. Romos IM. Lipton MA. J. Org. Chem.  2006,  71:  6351 
  CrossrefGoogle Scholar
• 8 Krishnamoorthy R. Vazquez-Serrano LD. Tunk JA. Kowalski JA. Benson AG. Breaux NT. Lipton MA. J. Am. Chem. Soc.  2006,  128:  15392 
  CrossrefGoogle Scholar
• 9a Kolb HC. VanNieuwhenze M. Sharpless KB. Chem. Rev.  1994,  94:  2483 
  Google Scholar
• 9b Kwong H. Sorato C. Ogino Y. Chen H. Sharpless KB. Tetrahedron Lett.  1990,  31:  2999 
  Google Scholar
• 10a Bodkin JA. McLeod MD. J. Chem. Soc., Perkin Trans. 1  2002,  2733 
  CrossrefGoogle Scholar
• 10b O’Brien P. Angew. Chem. Int. Ed.  1999,  38:  326 
  CrossrefGoogle Scholar
• 10c Tao B. Schlingloff G. Sharpless KB. Tetrahedron Lett.  1998,  39:  2507 
  CrossrefGoogle Scholar
• 10d Li G. Chang H.-T. Sharpless KB. Angew. Chem., Int. Ed. Engl.  1996,  35:  451 
  CrossrefGoogle Scholar
• 11 O’Brian P. Osborne SA. Parker D. Tetrahedron Lett.  1998,  39:  4099 
  CrossrefGoogle Scholar
• 12a Cao B. Park H. Joullié MM. J. Am. Chem. Soc.  2002,  124:  520 
  CrossrefGoogle Scholar
• 12b Park H. Cao B. Joullié MM. J. Org. Chem.  2001,  66:  7223 
  CrossrefGoogle Scholar
• 13 Fleming PA. Sharpless KB. J. Org. Chem.  1991,  56:  2869 
  CrossrefGoogle Scholar
• 14 Xiong C. Wang W. Hruby V. J. Org. Chem.  2002,  67:  3514 
  CrossrefGoogle Scholar
• 15 Carpino LA. Imazumi H. El-Faham A. Ferrer FJ. Zhang C. Lee Y. Foxman BM. Henklein P. Hanay C. Mügge C. Wenschuh H. Klose J. Beyerman M. Bienert M. Angew. Chem. Int. Ed.  2002,  41:  441 
  CrossrefGoogle Scholar
• 16 Carpino LA. J. Am. Chem. Soc.  1993,  115:  4397 
  CrossrefGoogle Scholar
• 17 Dale JA. Mosher HS. J. Am. Chem. Soc.  1973,  95:  512 
  CrossrefGoogle Scholar
• 18 Recently, Cranfill and Lipton reported the synthesis of (2R,3R)-β-MeOTyr using Evans aziridination with chiral bis(oxazoline)copper complex: Cranfill DC. Lipton MA. Org. Lett.  2007,  9:  3511 
  Google Scholar