The article reports a convergent and efficient total synthesis of (+)-heilonine, a C-nor D-homo steroidal alkaloid with a hexacyclic ring system, nine stereocenters, and a trans-hydrindane moiety. The synthesis involves four selective C–H functionalizations to form key C–C bonds and stereocenters, a Stille carbonylative cross-coupling to connect the AB and DEF ring systems, and a Nazarov cyclization to construct the five-membered C ring. These transformations significantly reduce functional group manipulations and achieve the synthesis of (+)-heilonine in 11 or 13 longest linear sequence (LLS) steps. The synthesis begins with the Wieland–Miescher ketone and phenylacetylene, and the final product is obtained in high yield. The study highlights the importance of transition metal catalysis and C–H functionalization chemistry in the efficiency of natural product synthesis.The article reports a convergent and efficient total synthesis of (+)-heilonine, a C-nor D-homo steroidal alkaloid with a hexacyclic ring system, nine stereocenters, and a trans-hydrindane moiety. The synthesis involves four selective C–H functionalizations to form key C–C bonds and stereocenters, a Stille carbonylative cross-coupling to connect the AB and DEF ring systems, and a Nazarov cyclization to construct the five-membered C ring. These transformations significantly reduce functional group manipulations and achieve the synthesis of (+)-heilonine in 11 or 13 longest linear sequence (LLS) steps. The synthesis begins with the Wieland–Miescher ketone and phenylacetylene, and the final product is obtained in high yield. The study highlights the importance of transition metal catalysis and C–H functionalization chemistry in the efficiency of natural product synthesis.