4.5 Article

Total Synthesis and Structural Revision of (-)-ProtubonineA and (-)- Protubonine B

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 12, Pages 2557-2564

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201400029

Keywords

Total synthesis; Natural products; Alkaloids; Nitrogen heterocycles; Configuration determination

Funding

  1. Spanish Ministerio de Economia y Competitividad (MINECO) [SAF2010-17935-FEDER]
  2. Xunta de Galicia [08CSA052383PR]

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The proposed structures of (-)-protubonine A and (-)-protubonine B, which are pyrrolidinoindoline diketopiperazine alkaloids that were isolated from the marine-derived fungus Aspergillus sp. SF-5044, have been synthesized and correspond to diastereomers of the natural isolates. The total syntheses, herein, established the stereostructures of the alkaloids as the C-11 epimers of the purported structures.

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