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Synlett 1991; 1991(4): 283-284
DOI: 10.1055/s-1991-20709
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Stereoselective Synthesis of the C13-C19 Fragment of the Cytotoxic Marine Products Calyculins; Part 11

Osamu Hara* , Yasumasa Hamada, Takayuki Shioiri
  • *Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467, Japan
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Publication Date:
07 March 2002 (online)

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The stereoselective synthesis of the C13-C19 fragment 2b [(7S)-hexahydro-5-hydroxy-7-methoxy-3,3-dimethyl-2-oxofuro-[3,2-b]pyran] of the cytotoxic marine products calyculins (1 or their antipodes) from potassium (R)-2,3-O-isopropylideneglycerate (3) has been completed utilizing stereoselective hydrogenation of the 5-substituted tetronic acid derivative 8 [(5S)-5-(tert-butyldimethylsiloxymethyl)-4-hydroxy-3-methyl-2(5H)-furanone] and the stereoselective allylation of the furanose aldehyde 12 [(2S,3R)-3-benzyloxy-5-methoxy-4,4-dimethyltetrahydrofuran-2-carbaldehyde].