Effective and Versatile Synthesis of Ginkgotoxin and Its 4′-O-Derivatives through Regioselective 4′-O-Alkylation and 4′-O-Chlorination of 3,5′-O-Dibenzylpyridoxine,SynOpen

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Effective and Versatile Synthesis of Ginkgotoxin and Its 4′-O-Derivatives through Regioselective 4′-O-Alkylation and 4′-O-Chlorination of 3,5′-O-Dibenzylpyridoxine
SynOpen ( IF 2.0 ) Pub Date : 2020-08-14 , DOI: 10.1055/s-0040-1707242
Yan Zhang _{1,

2} , Boshi Huang ₁ , Richmond Danso-Danquah _{1,

2} , Martin K. Safo _{1,

2}

Affiliation

A regioselective synthesis of ginkgotoxin and its derivatives is described. A blocking–deblocking strategy was employed in this new methodology, which relied on selective ketal protection of the 3- and 4′-hydroxy groups of pyridoxine. The key intermediate, O-dibenzylpyridoxine, was prepared in four steps with a reasonable yield. The present synthetic route enables convenient and versatile preparation of diversified 4′-substituted pyridoxine derivatives.

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