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ChemInform Abstract: An Epoxide Rearrangement — Radical Rearrangement Approach to 6-Substituted 2-Azabicyclo[2.2.1]-5-heptenes: Synthesis of an Epibatidine Analogue.

✍ Scribed by David M. Hodgson; Christopher R. Maxwell; Ian R. Matthews

Publisher: John Wiley and Sons
Year: 2010
Weight: 31 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199914255

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✦ Synopsis

An Epoxide Rearrangement -Radical Rearrangement Approach to 6-Substituted 2-Azabicyclo[2.2.1]-5-heptenes: Synthesis of an Epibatidine Analogue.

-Base-promoted isomerization of the epoxide (I) provides the azanortricyclanol (II). The latter can be readily converted to the derivatives (V) as precursors for a novel free radical induced rearrangement. The 6-substituted 2-azabicyclo[2.2.1]-5-heptenes (VI) are obtained; (VIc) is conveniently transformed to compound (VII) as an analogue of epibatidine. -

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