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Synthesis 1993; 1993(9): 903-908
DOI: 10.1055/s-1993-25967
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Iterative Methodology for the Stereocontrolled Synthesis of Polyol Chains Employing 2-Acetylthiazole as Lactaldehyde Equivalent

Alessandro Dondoni* , Pedro Merino
  • *Dipartimento di Chimica, Laboratorio di Chimica Organica, Università via Borsari 46, I-4410 Ferrara, Italy
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Publication Date:
29 April 2002 (online)

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The anti-diastereoselective addition (ds 90-92%) of the lithium enolate of 2-acetylthiazole to chiral (poly)alkoxy aldehydes and the stereocontrolled ketone reduction of the resultant aldols using diisobutylaluminum hydride/tetramethylammonium triacetoxyborohydride followed by the aldehyde unmasking from the thiazolering, afford three-carbon higher homologue aldehydes bearing a syn-or anti-1,3-diol unit. The iterative repetition of the sequence provides a route to polyhydroxylated chains having 1,3- and 1,2-diol units. In this methodology 2-acetylthiazole serves as the surrogate of lactaldehyde and its lithium enolate as the equivalent of the α-hydroxypropanal β-anion synthon.