Tetrahedron

Stereoelectronic and steric control in chiral cyclohexane synthesis toward (−)-tetrodotoxin

M Bamba, T Nishikawa, M Isobe

文献索引：Bamba, Makoto; Nishikawa, Toshio; Isobe, Minoru Tetrahedron, 1998 , vol. 54, # 24 p. 6639 - 6650

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被引用次数: 19

摘要

The synthesis of important intermediates for tetrodotoxin has been explored. The chiral cyclohexane ring was constructed by electrocyclization from a triene precursor and by conversion to the highly oxygenated cyclohexane ring. In particular, the introduction of an α- hydroxy group at the 5 position (toxin-numbering) in tetrodotoxin was achieved by allylic oxidation with SeO2.