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Regioselective electrophilic oxidation of a 5-amino-endo-tricyclo[5.2.1.02,6]decenyl enaminone. Synthesis of a novel heterocyclic compound

✍ Scribed by Namakkal G Ramesh; Antonius J.H Klunder; Binne Zwanenburg

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 78 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01636-7

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✦ Synopsis

An unexpected tandem regioselective oxidation and cyclization of 5-((S)-2%-hydroxymethylpyrrolidin-1%-yl)-endo-tricyclo[5.2.1.0 2,6 ]deca-4,8-dien-3-ones 7 is reported. The reaction proceeds smoothly to afford novel tetracyclic compounds 8 and 9 in good yield, The structure of 8 was established by single-crystal X-ray analysis. Surprisingly, the C8 C9 norbornene double bond remains intact under these oxidative conditions.

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