Synlett 2009(11): 1861-1862  
DOI: 10.1055/s-0029-1217374
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Glyceraldehyde Acetonide - Recent Applications of this Chiron in Organic Synthesis

Evanoel Crizanto de Lima*
Laboratório de Química Bioorgânica (LQB), NPPN, Bl H, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, ­Cidade Universitária, CEP: 21941-590, Rio de Janeiro, Brazil
e-Mail: evanoel.crizanto@gmail.com;
Further Information

Publication History

Publication Date:
16 June 2009 (online)

Introduction

Glyceraldehyde acetonide (2,3-O-isopropylidene-d-gly­ceraldehyde, 1) it is a well-known chiron which has been used in organic synthesis for multiple purposes. [¹] It has been applied on the synthesis of a β-adrenergic antagonist, [²] on multicomponent reaction in the synthesis of ­nakadomarin A precursor, [³] and reacts with several organometallics to afford chiral alcohols used as precursors in total syntheses. [4-7] Its R isomer is easily prepared from selective protection and oxidative cleavage of ­in­expensive and available commercially d-mannitol (Scheme  [¹] ) [8] and its enantiomer can be obtained from vitamin C. [9] The present Spotlight emphasises recent applications of this chiron in organic synthesis in its R and S enantiomeric forms.

Scheme 1

    References

  • For a review, see:
  • 1 Jurczak J. Pikul S. Bauer T. Tetrahedron  1986,  42:  447 
  • 2 Wang N.-X. Yu A.-G. Wang G.-X. Zhang X.-H. Li Q.-S. Li Z. Synthesis  2007,  1154 
  • 3 Ahrendt KA. Williams RM. Org. Lett.  2004,  6:  4539 
  • 4 Fettes A. Carreira EM. J. Org. Chem.  2003,  68:  9274 
  • 5 Cossy J. Willis C. Bellosta V. BouzBouz S. J. Org. Chem.  2002,  67:  1982 
  • 6 Guaragna A. Napolitano C. DAlonzo D. Pedatella S. Palumbo G. Org. Lett.  2006,  8:  4863 
  • 7 Huckins JR. Vicente J. Rychnovsky SD. Org. Lett.  2007,  9:  4757 
  • 8a Earle MJ. Abdur-Rashid A. Priestley ND. J. Org. Chem.  1996,  61:  5697 
  • 8b Schmid CR. Bryant JD. Dowlatzedah M. Phillips JL. Prather DE. Schantz RD. Sear NL. Vianco CS. J. Org. Chem.  1991,  56:  4056 
  • 9a Hubschwerlin C. Synthesis  1986,  962 
  • 9b Mikkilineni AB. Kumar P. Abushanab E. J. Org. Chem.  1988,  53:  6005 
  • 10 Kim YJ. Lee D. Org. Lett.  2006,  8:  5219 
  • 11 Curti C. Zanardi F. Battistini L. Sartori A. Rassu G. Auzzas L. Roggio A. Pinna L. Casiraghi G. J. Org. Chem.  2006,  71:  225 
  • 12 Majewski M. Nowak P. J. Org. Chem.  2000,  65:  5152 
  • 13 Li G. van der Donk WA. Org. Lett.  2007,  9:  41 
  • 14 Kumaraswamy G. Markondaiah B. Tetrahedron  2008,  64:  5861 
  • 15 Sohtome Y. Kato Y. Handa S. Aoyama N. Nagawa K. Matsunaga S. Shibasaki M. Org. Lett.  2008,  10:  2231