Total Synthesis of the Biphenyl Alkaloid (−)-Lythranidine

Gebauer, Konrad; Fürstner, Alois

doi:10.1002/anie.201402550

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Total Synthesis of the Biphenyl Alkaloid (−)-Lythranidine

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Gebauer, Konrad
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Gebauer, K., & Fürstner, A. (2014). Total Synthesis of the Biphenyl Alkaloid (−)-Lythranidine. Angewandte Chemie International Edition, 53(25), 6393-6396. doi:10.1002/anie.201402550.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0019-DA6C-5

Abstract

A sequence comprising a ring-closing alkyne metathesis of a propargyl alcohol derivative, followed by a ruthenium-catalyzed redox isomerization of the derived cycloalkyne and a transannular aza-Michael addition allowed the formation of the distinguishing piperidine-metacyclophane framework of the Lythraceum alkaloid lythanidine in a few high-yielding steps. This application attests to the excellent functional-group tolerance of a molybdenum alkylidyne complex endowed with triphenylsilanolate ligands, which enabled the macrocyclization even in the presence of protic functionalities, and thus illustrates the power of contemporary catalytic acetylene chemistry for target-oriented synthesis.