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Synthesis of the himandrine skeleton

O'Connor, Patrick; Mander, Lewis; McLachlan, Matthew


The hexacyclic himandrine skeleton 5, which is present in the most complex alkaloids of the tropical rain forest tree Galbulimima belgraveana, has been prepared for the first time. The synthesis begins from the known [3.2.1]benzobicyclooctene intermediate 10. Key steps include a Diels-Alder cycloaddition, Curtius rearrangement, Birch reduction, an intramolecular nucleophilic amination, and a palladium-mediated alkene amination.

CollectionsANU Research Publications
Date published: 2004
Type: Journal article
Source: Organic Letters
DOI: 10.1021/ol036308n


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