A new entry to Amaryllidaceaealkaloids from carbohydrates: total synthesis of (+)-vittatine

Abstract

The stereoselective and chiral synthesis of the Amaryllidaceae alkaloid, (+)-vittatine 1, is described; the quaternary carbon in 1 was generated by Claisen rearrangement of a cyclohexenol derived from D-glucose by way of a Ferrier's carbocyclisation reaction and a hexahydroindole skeleton was effectively constructed by intramolecular aminomercuration–demercuration, followed by Chugaev reaction.