Norsecurinamine B represents the first example of an NH-bridged dimeric Securinega alkaloid, in which two norsecurinine monomers are joined through an amine linker at their endo faces. However, the exo face of norsecurinine is intrinsically favored for nucleophilic attack, rendering the synthesis of the target challenging. Herein, we disclose a convergent total synthesis of norsecurinamine B, highlighting the strategic design elements that effectively address this stereochemical challenge.