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Synthesis 2010(18): 3063-3066  
DOI: 10.1055/s-0030-1258185
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

A Concise Synthesis of (2S,3S,4S)-2-(Hydroxymethyl)pyrrolidine-3,4-diol (LAB1)

Puspesh K. Upadhyay, Pradeep Kumar*
Division of Organic Chemistry, National Chemical Laboratory, Pune 411 008, India
Fax: +91(2)25902629; e-Mail: pk.tripathi@ncl.res.in;
Further Information

Publication History

Received 25 May 2010
Publication Date:
16 July 2010 (online)

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Abstract

The synthesis of (2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol (LAB1) from Garner’s aldehyde is described using the Sharpless asymmetric dihydroxylation as the key step.

Key words

Garner’s aldehyde - Wittig reaction - diastereoselectivity - alkaloid - azasugars - pyrrolidine

    References

  • 1 Asano N. Nash RJ. Molyneux RJ. Fleet GWJ. Tetrahedron: Asymmetry  2000,  11:  1645 
    CrossrefGoogle Scholar
  • 2 El Ashry ESH. Rashed N. Shobier AHS. Pharmazie  2000,  55:  331 
    Google Scholar
  • 3 El Nemr A. Tetrahedron  2000,  56:  8579 
    CrossrefGoogle Scholar
  • 4a Coppola GM. Huster HF. Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids   Wiley; New York: 1987. 
    Google Scholar
  • 4b Jurczak J. Golebiowski A. Chem. Rev.  1989,  89:  149 
    Google Scholar
  • 4c Golebiowski A. Jurczak J. Total Synthesis of Linocomycin and Related Chemistry, In Recent Progress in the Chemical Synthesis of Antibiotics   Springer; Berlin: 1990. 
    Google Scholar
  • 4d Reetz MT. Angew. Chem., Int. Ed. Engl.  1991,  30:  1531 
    Google Scholar
  • 4e Dondoni A. Carbohydrate Synthesis via Thiazoles, In Modern Synthetic Reactions   Vol. 2:  Scheffold R. Verlag Helvetica Chimica Acta; Basel: 1992.  p.377 
    Google Scholar
  • 5 Jurczak J. Golebiowski A. The Synthesis of Antibiotic Amino Sugars from α-Amino Aldehydes, In Antibiotics and Antiviral Compounds, Chemical Synthesis and Modification   Krohn K. Kirst H. Maag H. VCH; Weinheim: 1993. 
    Google Scholar
  • 6 Jurczak J. Golebiowski A. From α-Amino Acids to Amino Sugars, In Studies in Natural Products Chemistry   Vol. 4:  . Elsevier; Amsterdam: 1989. 
    Google Scholar
  • 7 Golebiowski A. Jurczak J. Synlett  1993,  241 
    Article in Thieme ConnectGoogle Scholar
  • 8 Kiciak K. Jacobsson U. Golebiowski A. Jurczak J. Pol. J. Chem.  1993,  67:  685 
    Google Scholar
  • 9a Fleet GWJ. Witty DR. Tetrahedron: Asymmetry  1990,  1:  119 
    Google Scholar
  • 9b Hosaka A. Ichikawa S. Shindo H. Sato T. Bull. Chem. Soc. Jpn.  1989,  62:  797 
    Google Scholar
  • 9c Mulzer J. Becker R. Brunner E. J. Am. Chem. Soc.  1989,  111:  7500 
    Google Scholar
  • 9d Abiko A. Roberts JC. Takemasa T. Masamune S. Tetrahedron Lett.  1986,  27:  4536 
    Google Scholar
  • 9e Zanardi F. Battistini L. Nespi M. Rassu G. Spanu P. Cornia M. Casiraghi G. Tetrahedron: Asymmetry  1996,  7:  1167 
    Google Scholar
  • 9f Fleet GWJ. Son JC. Tetrahedron  1988,  44:  2637 
    Google Scholar
  • 9g Weir CA. Taylor CM. J. Org. Chem.  1999,  64:  1554 
    Google Scholar
  • 9h Chen SY. Joullie MM. Tetrahedron Lett.  1983,  24:  5027 
    Google Scholar
  • 9i Bols M. Lundt I. Acta Chem. Scand.  1992,  46:  298 
    Google Scholar
  • 9j Kim HJ. Lee WS. Yang MS. Lee SG. Park KH. Synlett  1999,  614 
    Google Scholar
  • 9k Kim IS. Zee OP. Jung YH. Org. Lett.  2006,  8:  4101 
    Google Scholar
  • 10a Karl J.-U. Wieland T. Liebigs Ann. Chem.  1981,  1445 
    Google Scholar
  • 10b Durand J.-O. Larchevêque M. Petit Y. Tetrahedron Lett.  1998,  39:  5743 
    Google Scholar
  • 10c Arakawa Y. Yoshifuji S. Chem. Pharm. Bull.  1991,  39:  2219 
    Google Scholar
  • 10d Humphrey AJ. Parsons SF. Smith MEB. Turner NJ. Tetrahedron Lett.  2000,  41:  4481 
    Google Scholar
  • 10e Hulme AN. Montgomery CH. Henderson DK. J. Chem. Soc., Perkin Trans. 1  2000,  1837 
    Google Scholar
  • 10f Huwe CM. Blechert S. Synthesis  1997,  61 
    Google Scholar
  • 10g Goli DM. Cheesman BV. Hassan ME. Lodaya R. Slama JT. Carbohydr. Res.  1994,  259:  219 
    Google Scholar
  • 10h Ribes C. Falomir E. Carda M. Marco JA. J. Org. Chem.  2008,  73:  7779 ; and references cited therein
    Google Scholar
  • 11a Jones DWC. Nash RJ. Bell EA. Williams JM. Tetrahedron Lett.  1985,  26:  3125 
    Google Scholar
  • 11b Dhavale DD. Kumar KSA. Chaudhari VD. Sharma T. Sabharwal SG. Reddy JP. Org. Biomol. Chem.  2005,  3:  3720 
    Google Scholar
  • 11c Sugiyama M. Hong Z. Liang P.-H. Dean SM. Whalen LJ. Greenberg WA. Wong C.-H. J. Am. Chem. Soc.  2007,  129:  14811 
    Google Scholar
  • 11d Huang Y. Dalton DR. J. Org. Chem.  1997,  62:  372 
    Google Scholar
  • 11e Zhou X. Liu W.-H. Ye J.-L. Huang P.-Q. Tetrahedron  2007,  63:  6364 
    Google Scholar
  • 11f Lombardo M. Fabbroni S. Trombini C. J. Org. Chem.  2001,  66:  1264 
    Google Scholar
  • 12a Pandey SK. Kumar P. Synlett  2007,  2894 
    Google Scholar
  • 12b Pandey SK. Kumar P. Tetrahedron Lett.  2005,  46:  4091 
    Google Scholar
  • 12c Cherian SK. Kumar P. Tetrahedron: Asymmetry  2007,  18:  982 
    Google Scholar
  • 12d Kandula SV. Kumar P. Tetrahedron  2006,  62:  9942 
    Google Scholar
  • 12e Kumar P. Bodas MS.
    J. Org. Chem.  2005,  70:  360 
    Google Scholar
  • 12f Bodas MS. Upadhyay PK. Kumar P. Tetrahedron Lett.  2004,  45:  987 
    Google Scholar
  • 12g Upadhyay PK. Prasad R. Pandey M. Kumar P. Tetrahedron Lett.  2009,  50:  2440 
    Google Scholar
  • 13a Garner P. Park JM. J. Org. Chem.  1987,  52:  2361 
    Google Scholar
  • 13b Garner P. Park JM. Org. Synth.  1991,  70:  18 
    Google Scholar
  • 13c Garner P. Ramakanth S. J. Org. Chem.  1986,  51:  2609 
    Google Scholar
  • 13d Garner P. Park JM. Mallecki E. J. Org. Chem.  1988,  53:  4395 
    Google Scholar
  • 14a Kolb HC. VanNiewenhze MS. Sharpless KB. Chem. Rev.  1994,  94:  2483 
    Google Scholar
  • 14b Becker H. Sharpless KB. Angew. Chem., Int. Ed. Engl.  1996,  35:  448 
    Google Scholar
  • 15 Dondoni A. Merino P. Perrone D. Tetrahedron  1993,  49:  2939 
    CrossrefGoogle Scholar