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The strategy begins with alkylation of a chiral lactam and subsequent\n                    <jats:italic>N<\/jats:italic>\n                    \u2010oxidation via an imino ether to afford the\n                    <jats:italic>N<\/jats:italic>\n                    \u2010hydroxylactam. For the key transformation to functionalize the amide carbonyl, an iridium\u2010catalyzed reductive [3\u00a0+\u00a02] cycloaddition of the\n                    <jats:italic>N<\/jats:italic>\n                    \u2010hydroxylactam provides a tricyclic isoxazolidine in a one\u2010pot process. After the coupling reaction with an allylic silane fragment, the total synthesis is accomplished through intramolecular Hosomi\u2013Sakurai allylation to construct a pentacyclic core. 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