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A Total Synthesis of (±)-Leuconodines D and E

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journal contribution
posted on 02.10.2019 by Jing Zhang, Fu-She Han
A new synthetic route for a short synthesis of (±)-leuconodines D and E was developed. The rapid construction of the diaza[]­fenestrane core was achieved through a sequence involving a Pd-catalyzed aerobic oxidative Heck cross-coupling reaction for the construction of indole δ-lactam containing a full-carbon quaternary center, an epoxidative cyclization for the assembly of pyrroloindole, and a ring-closing metathesis for the construction of the piperidine ring. As a result, the total synthesis of (±)-leuconodine E (2) was achieved for the first time within a 10-step linear sequence, and a more concise total synthesis of (±)-leuconodine D (1) was accomplished within a 12-step linear sequence from the commercially available tryptophol.