Retro-biosynthetic construction of corynanthe alkaloid skeletons from rhynchophylline alkaloids?

Organic & Biomolecular Chemistry Pub Date: 2019-08-14 DOI: 10.1039/C9OB01740B

Abstract

Rhynchophylline alkaloids are bio-synthesized from corynanthe alkaloids via an oxidative rearrangement. We demonstrate here that corynanthe alkaloids could be generated from rhynchophylline alkaloids in a retro-biosynthetic manner via a Wagner–Meerwein rearrangement. A series of corynanthe analogues were afforded with good functional group tolerance and satisfactory yields.

Graphical abstract: Retro-biosynthetic construction of corynanthe alkaloid skeletons from rhynchophylline alkaloids
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