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Synlett 1992; 1992(2): 151-152
DOI: 10.1055/s-1992-21298
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A Synthesis of the Oxazole Part of Calyculins; Part 2

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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A synthesis of methyl 2-[(1R,3S)-(3-butoxycarbonylamino) -1-methylbutyl]-1,3-oxazole-4-carboxylate (2) corresponding to the antipode of the oxazole part of calyculins C, D, G, and H (1), potent cytotoxic substances from a marine sponge, has been accomplished from meso-2,4-dimethylglutaric anhydride (3).The method involves the asymmetric ring opening of the prochiral cyclic anhydride with L-O-tert-butyldimethylsilylserine methyl ester.

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