The total synthesis of rac-o-methyljoubertiamine

The Claisen-Eschenmoser3.3]sigmatropic rearrangement¹ of appropriately functionalized 3-aryl-2-cyclohexenols provides a ready synthesis of mesembrane alkaloids.^2,3 Herein we describe the total synthesis of rac-O-methyljoubertiamine⁴¹ (1) as part of the development of a general synthetic route to these alkaloids, involving the aforementioned rearrangement as the key synthetic step.