Journal of Organic Chemistry p. 1056 - 1064 (1988)
Update date:2022-08-11
Topics:
Palmisano, Giovanni
Danieli, Bruno
Lesma, Giordano
Trupiano, Federica
Pilati, Tullio
β-Anilinoacrylate Aspidosperma alkaloids vincadifformine (2a) and tabersonine (2b) react with Fremy's salt in aqueous acidic conditions via radical coupling at C-16.The resulting zwitterionic compounds 7a and 10 rearange to isoxazolidines 8 and then ultimately to azepino<2,3-b>indoles 9.The mechanism of these reactions is discussed, and the structures of 7a, 8b, and 9a were established by single-crystal X-ray analysis.Diazotization of amine 20b (X = NH2) affords fragmentation-cyclization products corresponding to eburnanes 18 and 21.This reaction mimics the skeletal rearrangement of Aspidosperma -> Hunteria alkaloids, and these findings support Wenkert's biogenetic proposal.
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