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Synthesis 2007(24): 3846-3850  
DOI: 10.1055/s-2007-990936
PAPER
© Georg Thieme Verlag Stuttgart · New York

Stereochemical Assignments for All Four Isomers of Dolaproine via Lactam Formation

Xiao Shang*, Minh Nguyen, Nathan C. Ihle
Process Chemistry, Seattle Genetics, Inc., 21823 30th Drive SE, Bothell, WA 98021, USA
Fax: +1(425)5274755; e-Mail: xshang@seagen.com;
Further Information

Publication History

Received 20 April 2007
Publication Date:
28 November 2007 (online)

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Abstract

The stereochemistry of all four possible stereoisomers of dolaproine was established through the syntheses and spectral analyses of structurally rigid bicyclic lactams. In addition, discrepancies with an earlier report were discovered and corrections are provided.

Key words

dolastatin - dolaproine - auristatin - aldol reaction - lactam - stereochemical - coupling constant - NOE

    References

  • 1a Pettit GR. Kamano Y. Herald CL. Tuinman AA. Boettner FE. Kizu H. Schmidt JM. Baczynskyj L. J. Am. Chem. Soc.  1987,  109:  6883 
    Google Scholar
  • 1b Madden T. Tran HT. Beck D. Huie R. Newman RA. Pusztai L. Wright JJ. Abbruzzese JL. J. Clin. Oncol.  2000,  6:  1293 
    Google Scholar
  • 2a Doronina SO. Toki BE. Torgov MT. Mendelsohn BA. Cerveny CG. Chace DF. DeBlanc RL. Gearing RP. Bovee TD. Siegall CB. Francisco JA. Wahl AF. Meyer DL. Senter PD. Nature Biotechnol.  2003,  21:  778 
    CrossrefGoogle Scholar
  • 2b Doronina SO. Mendelsohn BA. Bovee TD. Cerveny CG. Alley SC. Meyer DL. Oflazoglu E. Toki BE. Sanderson RJ. Zabinski RF. Wahl AF. Senter PD. Bioconjugate Chem.  2006,  17:  114 
    CrossrefGoogle Scholar
  • 3a Pettit GR. Singh SB. Hogan F. Lloyd-Williams P. Herald DL. Burkett DD. Clewlow PJ. J. Am. Chem. Soc.  1989,  111:  5463 
    CrossrefGoogle Scholar
  • 3b Pettit GR. Barkóczy J. Srirangam JK. Singh SB. Herald DL. Williams MD. Kantoci D. Hogan F. Groy TL. J. Org. Chem.  1994,  59:  2935 
    CrossrefGoogle Scholar
  • 3c Pettit GR. Srirangam JK. Herald DL. Hamel E. J. Org. Chem.  1994,  59:  6127 
    CrossrefGoogle Scholar
  • 4a Hamada Y. Hayashi S. Shioiri T. Tetrahedron Lett.  1991,  32:  931 
    CrossrefGoogle Scholar
  • 4b Hayashi K. Hamada Y. Shioiri T. Tetrahedron Lett.  1991,  32:  7287 
    CrossrefGoogle Scholar
  • 4c Tomioka K. Kanai M. Koga K. Tetrahedron Lett.  1991,  32:  2395 
    CrossrefGoogle Scholar
  • 4d Roux F. Maugras I. Poncet J. Niel G. Jouin P. Tetrahedron  1994,  50:  5345 
    CrossrefGoogle Scholar
  • 4e Pettit GR. Grealish MP. J. Org. Chem.  2001,  66:  8640 
    CrossrefGoogle Scholar
  • 4f Almeida W. Coelho F. Tetrahedron Lett.  2003,  44:  937 
    CrossrefGoogle Scholar
  • 5a Mordant C. Reymond S. Ratovelomanana-Vidal V. Genet J.-P. Tetrahedron  2004,  60:  9715 
    CrossrefPubMedGoogle Scholar
  • 5b Lavergne D. Mordant C. Ratovelomanana-Vidal V. Genet J.-P. Org. Lett.  2001,  3:  1909 
    CrossrefPubMedGoogle Scholar
  • 6 Pettit GR. Singh SB. Herald DL. Lloyd-Williams P. Kantoci D. Burkett DD. Barkoczy J. Hogan F. Warlaw TR. J. Org. Chem.  1994,  59:  6287 
    CrossrefGoogle Scholar
  • 8a

    See: http://www.casper.organ.su.se/ke3690/jhh.html (accessed 9 November 2007).
    Crossref
  • 8b Pretsch E. Buhlmann P. Affolter C. Structure Determination of Organic Compounds   3rd ed.:  Springer; Berlin: 2000.  p.167 
    CrossrefGoogle Scholar
  • 8c Karplus M. J. Am. Chem. Soc.  1963,  85:  2870 
    CrossrefGoogle Scholar
7

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