Elsevier

Tetrahedron Letters

Volume 55, Issue 44, 29 October 2014, Pages 6077-6080
Tetrahedron Letters

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

https://doi.org/10.1016/j.tetlet.2014.09.036Get rights and content

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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Acknowledgments

This work was financially supported by the Scientific Research on Innovative Areas, Chemical Biology of Natural Products, from MEXT-Japan (Grant No. 23102009) and JSPS KAKENHI-Japan (Grant Nos. 23228001 and 25282233).

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