Use of 1,3-dibenzyl-dihydrouracil in the chain extension of 2,3-O-isopropylidene-D-glyceraldehyde (Articolo in rivista)

Type
Label
  • Use of 1,3-dibenzyl-dihydrouracil in the chain extension of 2,3-O-isopropylidene-D-glyceraldehyde (Articolo in rivista) (literal)
Anno
  • 2003-01-01T00:00:00+01:00 (literal)
Alternative label
  • Fausta Ulgheri, John Bacsa, Luigi Nassimbeni, Pietro Spanu (2003)
    Use of 1,3-dibenzyl-dihydrouracil in the chain extension of 2,3-O-isopropylidene-D-glyceraldehyde
    (literal)
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  • Fausta Ulgheri, John Bacsa, Luigi Nassimbeni, Pietro Spanu (literal)
Pagina inizio
  • 671 (literal)
Pagina fine
  • 675 (literal)
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  • impact factor 2002 della rivista: 2.357 (literal)
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  • 44 (literal)
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  • In the synthesis of enantiomerically pure bioactive molecules, the synthetic strategy involving as a key operation the diastereoselective carbon-carbon bond formation between heterocyclic compounds and homochiral aldehydo or imino sugars has been widely used. For this purpose, we decided to explore the potentialities of dihydrouracil as a new homologating reagent both because of the biological importance of dihydropyrimidinone derivatives or because of the interest that C-glycosylated dihydropyrimidinones have shown as C-linked glycoside analogues of N-linked natural products. In the paper we report a simple and stereodivergent homologating approach to 5-trihydroxypropyl-dihydrouracil derivatives based on the aldol-type addition of DBDHU (1,3-dibenzyl-dihydrouracil) 2 to 2,3- O-isopropylidene-D-glyceraldehyde 3 . In order to evaluate the synthetic potentialities of this procedure for the synthesis of biologically interesting molecules, the stereoselective synthesis of b-ureido polyols was realized. In summary, in this paper we have shown the first use of dihydrouracil as a new homologating reagent for the chain extension of isopropylidene protected glyceraldehyde. Enantiomerically pure 5-trihydroxypropyl-DHU derivatives have been synthesized in good yields and diastereoselectivity in a stereodivergent way. Starting from 5-substituted-DHU intermediates the synthesis of ureido polyols 8 and 10 was realized via the reductive heterocycle ring cleavage. (literal)
Note
  • ISI Web of Science (WOS) (literal)
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  • Ulgheri, Istituto di Chimica Biomolecolare CNR. Bacsa, University of Cape Town. Nassimbeni, University of Cape Town. Spanu, Istituto di Chimica Biomolecolare CNR (literal)
Titolo
  • Use of 1,3-dibenzyl-dihydrouracil in the chain extension of 2,3-O-isopropylidene-D-glyceraldehyde (literal)
Abstract
  • A simple and stereodivergent approach to 5-trihydroxypropyl-dihydrouracil derivatives based on the aldol-type addition of 1,3-dibenzyl-dihydrouracil lithium enolate to 2,3-O-isopropylidene-D-glyceraldehyde is reported. The reaction was investigated in different solvents and under Lewis acid catalysis in order to establish the stereochemical preferences. The synthesis of enantiomerically pure (5S,1'S,2'R)-5-trihydroxypropyl-dihydrouracil derivative and its C-5 epimer was realized in good yields and diastereoselectivity. The synthesis of ureido polyols was obtained via the reductive heterocycle ring cleavage of these intermediates. (literal)
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