Synthesis of the C1-C12 Fragment of Calyculin C
Research output: Contribution to journal › Article › Scientific › peer-review
- Latvian Institute of Organic Synthesis
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.
|Number of pages||11|
|Publication status||Published - 1 Jan 2019|
|MoE publication type||A1 Journal article-refereed|
- calyculins, natural products, Negishi and Heck coupling, Stille, Suzuki-Miyaura, syntheses of di- and polyenes, transition-metal-catalyzed cross-coupling