A synthetic sequence, starting from diacetoneglucose, is developed for optically active (4R)-2(dimethyl-t-butylsilyloxy)-4-oxo aldehyde (2). The key step is the regioselective palladium-catalysed allylation of malonate with the allylic acetate (4). The 4-oxo aldehyde (2) undergoes Ba(OH)2 cyclization to the optically active (4R)-4-(dimethyl-t-butylsilyloxy)cyclopent-2-enone derivative (1).
E. Mezzina, D. Savoia, E. Tagliavini, C. Trombini and A. Umani-Ronchi, J. Chem. Soc., Perkin Trans. 1, 1989, 845 DOI: 10.1039/P19890000845
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