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ChemInform Abstract: Total Synthesis of (-)-Strychnine via the Wieland—Gumlich Aldehyde.

✍ Scribed by Daniel Sole; Josep Bonjoch; Silvina Garcia-Rubio; Emma Peidro; Joan Bosch

Publisher: John Wiley and Sons
Year: 2010
Weight: 35 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199925196

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✦ Synopsis

Total Synthesis of (-)-Strychnine via the Wieland-Gumlich Aldehyde. -A novel synthesis of optically pure (-)-strychnine (XI) is presented involving the easy generation of enantiopure octahydroindolone (III), the palladium-catalyzed piperidine ring closure with stereoselective incorporation of the E-hydroxyethylidene group into compound (V), and indoline ring closure by reductive cyclization of the α-(2-nitrophenyl) ketone moiety in compound (VII).

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