title: Stereocontrolled Synthesis of (-)-5,11-Dideoxytetrodotoxin.
abstract: New derivatives of an intriguing marine natural product are now accessible. The first asymmetric synthesis of the simple tetrodotoxin analogue, 5,11-dideoxytetrodotoxin (3), was achieved. Hydroxylation at position C8 of the key intermediate 1 relied on the neighboring trichloroacetamide group, and stereoselective elaboration of the vinyl group gave alpha-hydroxylactone 2, which was transformed into the title compound through a new guanidylation method.
authors.affiliation: Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601 (Japan).
authors.initials: T
authors.lastname: Nishikawa
authors.initials: M
authors.lastname: Asai
authors.initials: N
authors.lastname: Ohyabu
authors.initials: N
authors.lastname: Yamamoto
authors.initials: M
authors.lastname: Isobe