Toward the total synthesis of tetrodotoxin: stereoselective construction of the 7-oxanorbornane intermediate

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書誌事項

公開日
2014-10
資源種別
journal article
権利情報
  • https://www.elsevier.com/tdm/userlicense/1.0/
DOI
  • 10.1016/j.tetlet.2014.09.036
公開者
Elsevier BV

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説明

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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