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Total synthesis of (+/-)-strychnine via a [4 + 2]-cycloaddition/rearrangement cascade.

ABSTRACT: A new strategy for the synthesis of the Strychnos alkaloid (+/-)-strychnine has been developed and is based on an intramolecular [4 + 2]-cycloaddition/rearrangement cascade of an indolyl-substituted amidofuran. The critical D-ring was assembled by an intramolecular palladium-catalyzed enolate-driven cross-coupling of an N-tethered vinyl iodide. [reaction: see text].

SUBMITTER: Zhang H 

PROVIDER: S-EPMC2587098 | biostudies-literature | 2007 Jan

REPOSITORIES: biostudies-literature

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Total synthesis of (+/-)-strychnine via a [4 + 2]-cycloaddition/rearrangement cascade.

Zhang Hongjun H   Boonsombat Jutatip J   Padwa Albert A  

Organic letters 20070101 2

A new strategy for the synthesis of the Strychnos alkaloid (+/-)-strychnine has been developed and is based on an intramolecular [4 + 2]-cycloaddition/rearrangement cascade of an indolyl-substituted amidofuran. The critical D-ring was assembled by an intramolecular palladium-catalyzed enolate-driven cross-coupling of an N-tethered vinyl iodide. [reaction: see text]. ...[more]

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