Synthesis of the C1-C12 Fragment of Calyculin C

Olga V. Konstantinova, Ari M.P. Koskinen*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

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Abstract

Calyculins are a class of highly cytotoxic metabolites originally isolated from the marine sponge Discodermia calyx. To date, a total of twelve different calyculins (A-J) and calyculinamides (A, B and F) have been described, the most abundant (in D. calyx) being calyculins A and C. Herein, we demonstrate a concise route to access the C1-C12 tetraene fragment of calyculin C using transition-metal-catalyzed coupling reactions (Suzuki-Miyaura, Stille, Negishi and Heck) for the key connections. The synthesis starts from propionaldehyde and proceeds in 10 steps with 7.5% overall yield. We also describe an efficient route for the preparation of (Z)-3-iodobut-2-enenitrile in four steps and 68% yield.

Original languageEnglish
Pages (from-to)285-295
Number of pages11
JournalSynthesis (Germany)
Volume51
Issue number1
DOIs
Publication statusPublished - 1 Jan 2019
MoE publication typeA1 Journal article-refereed

Keywords

  • calyculins
  • natural products
  • Negishi and Heck coupling
  • Stille
  • Suzuki-Miyaura
  • syntheses of di- and polyenes
  • transition-metal-catalyzed cross-coupling

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