Toward the total synthesis of tetrodotoxin: stereoselective construction of the 7-oxanorbornane intermediate |
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Authors: | Atsushi Manabe Yasufumi OhfuneTetsuro Shinada |
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Institution: | Graduate School of Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan |
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Abstract: | The stereoselective synthesis of 7-oxanorbornane regarding as a key synthetic intermediate of tetrodotoxin (TTX) is reported. The bicyclo ring bearing various functional groups was successfully elaborated by a furan Diels–Alder (DA) reaction. The stereoselective installation of a quaternary amino carbon center to the DA product was achieved with the Tsuji–Trost allylation. The stereochemistry was unambiguously confirmed with X-ray. |
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Keywords: | Tetrodotoxin Diels&ndash Alder reaction Nitroolefin Furan |
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