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Synlett 1991; 1991(4): 285-286
DOI: 10.1055/s-1991-20710
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Stereoselective Synthesis of the C13-C19 Fragment of the Cytotoxic Marine Products Calyculins; Part 21

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 C13-C19 fragment of the cytotoxic marine products calyculins (1 or their antipodes) was stereoselectively prepared as the acyclic equivalent 2b [methyl (3R,4R,5S)-3,4-dibenzyloxy-5-methoxy-2,2-dimethyl-7-octenoate] from potassium (R)-2,3-O-isopropylideneglycerate (3) utilizing the stereoselective allylation of aldehyde 7 [(2S,3R)-2,3-dibenzyloxy-4,4-dimethyl-5-trityloxypentanal] in the presence of magnesium bromide.

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