4.8 Article

A Modular Approach to the Antifungal Sphingofungin Family: Concise Total Synthesis of Sphingofungin A and C

期刊

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202112616

关键词

antiparasitic activity; cross coupling; natural products; sphingofungins; total synthesis

资金

  1. German Research Foundation (DFG) [BE 4799/2-1]
  2. Leibniz Association
  3. European Union [802736]
  4. Projekt DEAL
  5. European Research Council (ERC) [802736] Funding Source: European Research Council (ERC)

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A synthetic approach towards the sphingofungin family was reported, yielding eight derivatives tested for antifungal, cell-proliferative, and antiparasitic activities, revealing structure-activity relations.
Sphingofungins are fungal natural products known to inhibit the biosynthesis of sphingolipids which play pivotal roles in various cell functions. Here, we report a short and flexible synthetic approach towards the sphingofungin family. Key step of the synthesis was a decarboxylative cross-coupling reaction of chiral sulfinyl imines with a functionalized tartaric acid derivative, which yielded the core motif of sphingofungins carrying four consecutive stereocenters and a terminal double bond. Subsequent metathesis reaction allowed for the introduction of different side chains of choice resulting in a total of eight sphingofungins, including for the first time sphingofungin C (eight steps from commercially available protected tartaric acid with an overall yield of 6 %) and sphingofungin A (ten steps). All newly synthesized derivatives were tested for their antifungal, cell-proliferative and antiparasitic activity unraveling their structure-activity relations.

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