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An asymmetric formal synthesis of trichodermamides B and C was achieved in 15 steps based on a tyrosine ester chiral-pool approach. Key features of this synthesis include stereoselective construction of a cis-1,2-oxazadecaline core by an acid-mediated tandem deprotection–intramolecular oxy-Michael reaction, oxime ether formation via an N-bromination–elimination sequence, and diene construction by a palladium-catalyzed demonomethylcarbonation.