First total synthesis of (+)-Membrine

Article abstract of DOI:10.1002/jlac.199719970616

The easily accessible, optically active diselenide 1 is converted into the chiral selenium electrophile 2 and used for oxyselenenylation reactions of alkenes with functionalized nucleophiles. This reaction allows the synthesis of addition products 4, 6 and 10 with the selenium functionality as precursors for an intramolecular radical cyclization. This strategy is applied to the first total synthesis of optically pure (+)-membrine (13) by a short synthetic sequence. VCH Verlagsgesellschaft mbH, 1997.