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Tricyclic core of manzamine B was successfully synthesized through asymmetric Diels–Alder reaction and RCM strategy. Cr–salen–F complex was found to be the most effective catalyst in DA reaction of aminodienes with heterocyclic dienophiles to give up to 97% ee. In the construction of 11-membered ring by RCM, first-Grubbs cat. gave better stereoselectivity.