The same approach can be employed to access swainsonine (3), a naturally occurring indolizidine alkaloid isolated from the fungal plant pathogen Rhizoctonia leguminicola. This natural product is a potent inhibitor of α-D-mannosidase and mannosidase II with anticancer and other useful biological activities that are most likely associated with its ability to inhibit the processing of glycoproteins. More than 40 syntheses of swainsonine have been reported to date that range in length from six to >20 steps (average approximately 14 steps). The shortest of these syntheses commences from 5-chloro-pentanal and involves an asymmetric chlorination that requires a low separation and multiple FG and redox manipulations. A recently reported improvement to this route relied on a similar logic utilizing a Rh-catalyzed Hayashi-type conjugate addition. In contrast, Ni-electrocatalytic cross-coupling of 17 with iodoarene 30 followed by ethylation arrives at intermediate 32 directly in high dr without protection of the OH group (two known steps are subsequently used to convert 32 to 33, see Supporting Information). From the standpoint of a medicinal chemistry effort this is attractive as SAR can be interrogated directly at the end of the synthesis through skeletal bond forming reactions (C-O and C-C).