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Synlett 1996; 1996(12): 1165-1167
DOI: 10.1055/s-1996-5729
DOI: 10.1055/s-1996-5729
letter
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Extensive Ring-Expansion Strategy for the Enantioselective Synthesis of the Medium Ring Ethers, Oxepene, Oxocane, and Oxonene, of Ciguatoxin
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Publication History
Publication Date:
31 December 2000 (online)
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