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Synlett 1994; 1994(1): 38-40
DOI: 10.1055/s-1994-22730
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Synthetic Studies of Halichondrin B, an Antitumor Polyether Macrolide Isolated from a Marine Sponge. 1. Stereoselective Synthesis of the C1-C13 Fragment via Construction of the B and A Rings by Kinetically and thermodynamically Controlled Intramolecular Michael Reactions.

K. Horita* , S. Hachiya, M. Nagasawa, M. Hikota, O. Yonemitsu
  • *Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060, Japan
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Publication Date:
22 March 2002 (online)

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A stereoselective synthesis of the C1-C13 fragment of halichondrin B starting from D-glucose is reported. Construction of 2,5-trans (B) and 2,5-cis substituted tetrahydropyran (A) rings using intramolecular Michael reactions under kinetical and thermodynamical conditions, respectively, were the critical steps.