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 language | English |
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Pages (from-to) | 285-295 |
Number of pages | 11 |
Journal | Synthesis (Germany) |
Volume | 51 |
Issue number | 1 |
DOIs | |
Publication status | Published - 1 Jan 2019 |
MoE publication type | A1 Journal article-refereed |
Keywords
- calyculins
- natural products
- Negishi and Heck coupling
- Stille
- Suzuki-Miyaura
- syntheses of di- and polyenes
- transition-metal-catalyzed cross-coupling