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Synthesis 2009(12): 2009-2014  
DOI: 10.1055/s-0029-1216824
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Cyclobutanols and Cyclopentane Dimers via Samarium(II) Iodide Induced Keto-Olefin Cyclisations of Carbohydrate-Derived Unsaturated Ketones

D. Bradley G. Williams*, Judy Caddy, Kevin Blann, J. J. Cronjé Grové, Cedric W. Holzapfel
Department of Chemistry, University of Johannesburg, P.O. Box 524, Auckland Park, Johannesburg 2006, South Africa
Fax: +27(11)4892819; e-Mail: bwilliams@uj.ac.za;
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Publikationsverlauf

Received 18 February 2009
Publikationsdatum:
19. Mai 2009 (online)

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Abstract

Some pentose and hexose sugars were converted into unsaturated ketone derivatives, which themselves served as substrates for 4-exo-trig radical cyclisation reactions mediated by SmI2. Depending on the order of addition of reagents, the keto-olefins could also be made to undergo a surprising tandem 5-endo-trig cyclisation/dimerisation reaction to a cyclopentane dimer or a cyclobutane monomer.

Key words

carbocycles - carbohydrates - radical reactions - samarium - ring closure

    References

  • 1 Ferrier RJ. Middleton S. Chem. Rev.  1993,  93:  2779 
    CrossrefGoogle Scholar
  • 2 Verheyden JPH. Richardson AC. Bhatt RS. Grant BD. Fitch WL. Moffat JG. Pure Appl. Chem.  1978,  50:  1363 
    CrossrefGoogle Scholar
  • 3a Grové JJC. Holzapfel CW. Williams DBG. Tetrahedron Lett.  1996,  37:  1305 
    Google Scholar
  • 3b Grové JJC. Holzapfel CW. Williams DBG. Tetrahedron Lett.  1996,  37:  5817 
    Google Scholar
  • 4a Williams DBG. Blann K. Eur. J. Org. Chem.  2004,  3286 
    Google Scholar
  • 4b Williams DBG. Caddy J. Carbohydr. Res.  2005,  340:  1301 
    Google Scholar
  • 4c Edmonds DJ. Muir KW. Procter DJ. J. Org. Chem.  2003,  68:  3190 
    Google Scholar
  • 4d Weinges K. Schmidbauer SB. Schick H. Chem. Ber.  1994,  127:  1305 
    Google Scholar
  • 5a Brown B. Hegedus LS. J. Org. Chem.  1998,  63:  8012 
    Google Scholar
  • 5b Martín-Vilà M. Minguillón C. Ortuño RM. Tetrahedron: Asymmetry  1998,  9:  4291 
    Google Scholar
  • 5c Godfrey JD, and Mueller RH. inventors; (Bristol-Myers Squibb Co.) US Patent  5773614.  ; Chem. Abstr. 1998, 129, 122668
  • 5d Maruyama T. Hanai Y. Sato Y. Snoeck R. Andrei G. Hosoya M. Balzarini J. De Clercq E. Chem. Pharm. Bull.  1993,  41:  516 
    Google Scholar
  • 5e Collins PW. Djuric SW. Chem. Rev.  1993,  93:  1533 
    Google Scholar
  • 5f Slusarchyk WA. Young MG. Bisacchi GS. Hockstein DR. Zahler R. Tetrahedron Lett.  1989,  30:  6453 
    Google Scholar
  • 5g Jacobs GA. Tino JA. Zahler R. Tetrahedron Lett.  1989,  30:  6955 
    Google Scholar
  • 6a Williams DBG. Caddy J. Blann K. Holzapfel CW. Synth. Commun.  2002,  32:  3755 
    Google Scholar
  • 6b Williams DBG. Blann K. Holzapfel CW. Synth. Commun.  2001,  31:  203 
    Google Scholar
  • 6c Williams DBG. Blann K. Holzapfel CW. J. Chem. Soc., Perkin Trans. 1  2001,  219 
    Google Scholar
  • 6d Williams DBG. Blann K. Holzapfel CW. J. Org. Chem.  2000,  65:  2834 
    Google Scholar
  • 7 Zhou Z. Bennet S. Tetrahedron Lett.  1997,  38:  1153 
    CrossrefGoogle Scholar
  • 8a Wanner MJ. Koomen GJ. Tetrahedron Lett.  1990,  31:  907 
    Google Scholar
  • 8b Barrett AGM. Broughton HB. Attwood SV. Gunatilaka LAA. J. Org. Chem.  1986,  51:  495 
    Google Scholar
  • 9 Dess DB. Martin JC. J. Org. Chem.  1983,  48:  4156 
    CrossrefGoogle Scholar
  • 10 Baldwin J. J. Chem. Soc., Chem. Commun.  1976,  734 
    CrossrefGoogle Scholar
  • 11a Molander GA. Czakó B. Rheam M. J. Org. Chem.  2007,  72:  1755 
    Google Scholar
  • 11b Molander GA. Harris CR. Tetrahedron  1998,  54:  3321 
    Google Scholar
  • 11c Molander GA. Harris CR. Chem. Rev.  1996,  96:  307 
    Google Scholar
  • 12 Bezzenine-Lafollée S. Guibé F. Villar H. Zriba R. Tetrahedron  2004,  60:  6931 
    CrossrefGoogle Scholar
  • 13 Johnston D. Couché E. Edmonds DJ. Muir KW. Procter DJ. Org. Biomol. Chem.  2003,  1:  328 
    CrossrefGoogle Scholar
  • 14 Caddy J. Williams DBG. Roodt A. Muller A. Acta Crystallogr., Sect. E  2003,  59:  o1095 
    CrossrefGoogle Scholar
  • 15 Blann K. Williams DBG. Roodt A. Muller A. Acta Crystallogr., Sect. E  2003,  59:  o1551 
    CrossrefGoogle Scholar
  • 17 Prasad E. Flowers RA. J. Am. Chem. Soc.  2002,  124:  6357 
    CrossrefGoogle Scholar
  • 18 Park S.-U. Varick TR. Newcomb M. Tetrahedron Lett.  1990,  31:  2975 
    CrossrefGoogle Scholar
  • 19 Johnston D. McCusker CM. Muir K. Procter DJ. J. Chem. Soc., Perkin Trans. 1  2000,  681 
    Google Scholar
  • 20 A recent review details the use of SmI2 in numerous asymmetric syntheses: Gopalaiah K. Kagan HB. New J. Chem.  2008,  32:  607 
    Google Scholar
  • 21a Cabrera A. Le Lagadec R. Sharma P. Arias JL. Toscano RA. Velasco L. Gaviño Alvarez C. Salmon M. J. Chem. Soc., Perkin Trans. 1  1998,  3609 
    Google Scholar
  • 21b Cabrera A. Alper H. Tetrahedon Lett.  1992,  33:  5007 
    Google Scholar
  • 21c Howells DM. Barker SM. Watson FC. Light ME. Hursthouse MB. Kilburn JD. Org. Lett.  2004,  6:  1943 
    Google Scholar
  • 22 Sadasivam DV. Antharjanam PKS. Prasad RJ. Flowers RA. J. Am. Chem. Soc.  2008,  130:  7228 
    CrossrefGoogle Scholar
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