The general approach for accessing to a tetracyclic hexahydro-3H-indolizino[8,7-b]indol-3-one alkaloids is that what involves the construction of the γ-lactam ring from a tricyclic precursor. Here in this report, we disclose a new synthetic strategy that permits the direct deconstruction of the tetracyclic indolo[2,3-a]quinolizine motif into the tetracyclic hexahydroindolizin-3-one scaffold of the naturally occurring (+)-cuscutamine without the use of either transition or precious metals. Additionally, the current total synthesis of both enantiomers provides structural clarification of the natural occurring alkaloid. © 2022 Wiley-VCH GmbH.