The recent isolation and characterization of a number of new alkaloids from the various SceZetiwn species of plants' has sparked the initiation of synthetic investigations which have culminated in the total syntheses of several of these alkaloids, including joubertiamine (:),*a O-methyljoubertiamine (?),' and mesembrine (_3).3 The presence of a quaternary carbon atom, the structural feature cormnon to these and most other alkaloids belonging to the SceZetiwn or the closely related bnaryZZiduceae families, renders the synthesis of these natural products a significant challenge. We have previously designed and developed several new synthetic procedures for the facile creation of quaternary l,R=H 2,R=Me 3, R=OMe 4, R=H carbon atoms from carbonyl compounds4 and have also described the successful application of one of these to the total synthesis of the spirosesquiterpene acorone. 5 We now wish to report an important extension of another of these methods to the synthesis of O-methyljoubertiamine (2) and the octahydroindolone 4. The key step in this new entry to the SceZetiwn and AmarytZiduceae alkaloids is the direct conversion of a carbonyl group to a nucleophilic, functional derivative of the homologous aldehyde, which may then be alkylated in situ, thereby completing the construction of the crucial quaternary carbon center. Since this synthetic strategy