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Synthesis of the C1-C12 Fragment of Calyculin C
| Content Provider | Semantic Scholar |
|---|---|
| Author | Konstantinova, Olga V. Koskinen, Ari M. P. |
| Copyright Year | 2019 |
| 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. |
| Starting Page | 285 |
| Ending Page | 295 |
| Page Count | 11 |
| File Format | PDF HTM / HTML |
| DOI | 10.1055/s-0037-1610387 |
| Alternate Webpage(s) | https://thieme-connect.com/products/ejournals/pdf/10.1055/s-0037-1610387.pdf |
| Alternate Webpage(s) | https://research.aalto.fi/files/30782264/CHEM_Koskinen_Konstantinova_Synthesis_of_the_C1_2019_Synthesis.pdf |
| Alternate Webpage(s) | https://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0037-1610387.pdf?issue=10.1055/s-008-42090 |
| Alternate Webpage(s) | https://www.thieme-connect.com/products/ejournals/pdf/10.1055/s-0037-1610387.pdf?issue=10.1055/s-008-42090 |
| Alternate Webpage(s) | https://www.thieme-connect.com/products/ejournals/pdf/10.1055/s-0037-1610387.pdf |
| Alternate Webpage(s) | https://doi.org/10.1055/s-0037-1610387 |
| Volume Number | 51 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
