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Synlett 1992; 1992(2): 149-150
DOI: 10.1055/s-1992-21297
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A Synthesis of the Oxazole Part of Calyculins; Part 1

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

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An efficient synthesis of 2-[(1R)-(3-butoxycarbonylamino) -1-methylpropyl]-1,3-oxazole-4-methanol (2)corresponding to the antipode of the oxazole part. [N(3)-C(26) part) of calyculins A, B, E, and F (1), potent cytotoxic substances from a marine sponge, has been accomplished from methyl (S)-3-hydroxy-2-methylpropionate (3).The method involves oxazoline formation followed by oxidation to the oxazole.

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