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The synthetic route begins with the development of an asymmetric double hydrogenation of 2,5-diketopiperazine-derived enamides enabled by a novel spiropyrrolidine-derived diphosphine (SPDP) ligand. Employment of mono- and oxidative Pictet\u2013Spengler cyclizations allows for expedient construction of the tetrahydroisoquinoline and benzo[3.3.1]-bridged rings along with an enamide alkene. At a late stage, an unprecedented stereochemical editing approach for direct \u03b2-epimerization of a primary alcohol was developed by virtue of borrowing hydrogen catalysis. 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