A convergent and efficient total synthesis of the C-nor D-homo steroidal alkaloid (+)-heilonine is reported, featuring 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. This approach significantly reduces functional group manipulations and delivers (+)-heilonine in 11 or 13 longest linear sequences (LLS) steps. Heilonine, isolated from Fritillaria ussuriensis Maxim., is a member of the Veratrum steroidal alkaloid family with a hexacyclic ring system, nine stereocenters, and a trans-hydrindane moiety. It has been studied for its therapeutic potential, including as an antitussive, sedative, and expectorant. Previous total syntheses of Veratrum alkaloids, such as jervine and veratramine, have been reported, but the synthesis of heilonine remains challenging due to its complex structure and multiple stereocenters. The current synthesis starts from the Wieland–Miescher ketone and phenylacetylene, utilizing C–H functionalizations and cross-coupling strategies to build the hexacyclic skeleton. Key steps include a Nazarov cyclization to form the C ring and a Stille carbonylative cross-coupling to connect the AB and DEF rings. The synthesis also involves the use of a tertiary amine and two secondary alcohols, with the axial secondary alcohol playing a role in stereocontrol. The final steps involve the reduction of a ketone to a methylene or secondary alcohol, leading to the isolation of (+)-heilonine in high yield. This work highlights the utility of transition metal catalysis and C–H functionalization in the efficient synthesis of complex natural products.A convergent and efficient total synthesis of the C-nor D-homo steroidal alkaloid (+)-heilonine is reported, featuring 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. This approach significantly reduces functional group manipulations and delivers (+)-heilonine in 11 or 13 longest linear sequences (LLS) steps. Heilonine, isolated from Fritillaria ussuriensis Maxim., is a member of the Veratrum steroidal alkaloid family with a hexacyclic ring system, nine stereocenters, and a trans-hydrindane moiety. It has been studied for its therapeutic potential, including as an antitussive, sedative, and expectorant. Previous total syntheses of Veratrum alkaloids, such as jervine and veratramine, have been reported, but the synthesis of heilonine remains challenging due to its complex structure and multiple stereocenters. The current synthesis starts from the Wieland–Miescher ketone and phenylacetylene, utilizing C–H functionalizations and cross-coupling strategies to build the hexacyclic skeleton. Key steps include a Nazarov cyclization to form the C ring and a Stille carbonylative cross-coupling to connect the AB and DEF rings. The synthesis also involves the use of a tertiary amine and two secondary alcohols, with the axial secondary alcohol playing a role in stereocontrol. The final steps involve the reduction of a ketone to a methylene or secondary alcohol, leading to the isolation of (+)-heilonine in high yield. This work highlights the utility of transition metal catalysis and C–H functionalization in the efficient synthesis of complex natural products.