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The total synthesis of the crinine alkaloid hamayne via a Pd[0]-catalyzed intramolecular Alder-ene reaction

Petit, Laurent; Banwell, Martin; Willis, Anthony


The racemic form of the title alkaloid, 1, has been prepared in 13 steps from the ring-fused gem-dibromocyclopropane 7. Key transformations include the thermally induced electrocyclic ring-opening of compound 7, the Pd[0]-catalyzed intramolecular Alder-ene (IMAE) reaction of the derived sulfonamide (±)-12, and the conversion of the ensuing C-3a-arylhexahydroindole (±)-16 into (±)-hamayne via a Pictet-Spengler reaction.

CollectionsANU Research Publications
Date published: 2011
Type: Journal article
Source: Organic Letters
DOI: 10.1021/ol2023938


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