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Synlett 1992; 1992(9): 705-707
DOI: 10.1055/s-1992-21460
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Synthesis of the AB Ring Fragment of Ciguatoxin: Ligand Controlled Regioselective Addition of Osmium Tetroxide to Double Bonds

Ohki Sato* , Masahiro Hirama
  • *Department of Chemistry, Faculty of Science, Tohoku University, Sendai 980, Japan
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Publication Date:
08 March 2002 (online)

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The AB ring fragment 4 {6-(3,4-dihydroxy-1-butenyl)-2,3,4,4a,9, 9a-hexahydro-6H-pyrano[3,2-b]oxepin} of ciguatoxin (1), which has a 3,4-dihydroxy-1-butenyl substituent, has been synthesized from the 6-(1,3-butadienyl) bicycle 3 corresponding to the AB ring segment of gambiertoxin 4B (2), a plausible metabolic precursor of 1, through ligand-controlled regioselective additions of osmium tetroxide to double bonds.

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