10-Step Asymmetric Total Synthesis and Stereochemical Elucidation of (+)-Dragmacidin D

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Abstract

The asymmetric synthesis of dragmacidin D (1) was completed in 10 steps. Its sole stereocenter was set by using direct asymmetric alkylation enabled by a C2-symmetric tetramine and lithium N-(trimethylsilyl)-tert-butylamide as the enolization reagent. A central Larock indole synthesis was employed in a convergent assembly of the heterocyclic subunits. The stereochemical evidence from this work strongly supports the predicted S configuration at the 6″ position, which is consistent with other members of the dragmacidin family of natural products.

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Jackson, J. J., Kobayashi, H., Steffens, S. D., & Zakarian, A. (2015). 10-Step Asymmetric Total Synthesis and Stereochemical Elucidation of (+)-Dragmacidin D. Angewandte Chemie - International Edition, 54(34), 9971–9975. https://doi.org/10.1002/anie.201504113

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