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Synlett 1996; 1996(12): 1165-1167
DOI: 10.1055/s-1996-5729
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Extensive Ring-Expansion Strategy for the Enantioselective Synthesis of the Medium Ring Ethers, Oxepene, Oxocane, and Oxonene, of Ciguatoxin

Tohru Oishi, Mitsuru Shoji, Kenji Maeda, Naomi Kumahara, Masahiro Hirama*
  • *Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-77, Japan, Fax 022-217-6566, E-mail hirama@ykbsc.chem.tohoku.ac.uk
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Publication Date:
31 December 2000 (online)

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The extensive ring-expansion strategy for the synthesis of oxepene 19, oxocane 23, and oxonene 28, which correspond to the D (E), I and F ring fragments of ciguatoxin (1), respectively, has been established. Chemoenzymatic asymmetric acylation of the meso alcohols using lipase AK provided a simple entry of the enantiomeric building blocks.

ciguatoxin - ring expansion - meso-compound - cyclic ether - lipase

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