Chemistry of Renieramycins. Part 14: Total Synthesis of Renieramycin I and Practical Synthesis of Cribrostatin 4 (Renieramycin H)
| Autor: | Naoki Saito, Masashi Yokoya, Mitsuhiro Sato, Keiichiro Kobayashi |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
Double bond
Stereochemistry Cribrostatin-4 Pharmaceutical Science Stereoisomerism selenium oxide oxidation Article Piperazines cribrostatin 4 (renieramycin H) chemistry.chemical_compound Haliclona structural determination Selenium Oxides Tetrahydroisoquinolines Drug Discovery Benzoquinones Organic chemistry Animals total synthesis lcsh:QH301-705.5 Pharmacology Toxicology and Pharmaceutics (miscellaneous) Piperazine marine natural product chemistry.chemical_classification biology Chemistry Total synthesis biology.organism_classification Isoquinolines lcsh:Biology (General) Yield (chemistry) Renieramycin I renieramycin I Derivative (chemistry) |
| Zdroj: | Marine Drugs Volume 13 Issue 8 Pages 4915-4933 Marine Drugs, Vol 13, Iss 8, Pp 4915-4933 (2015) |
| ISSN: | 1660-3397 |
| Popis: | The first total synthesis of (±)-renieramycin I, which was isolated from the Indian bright blue sponge Haliclona cribricutis, is described. The key step is the selenium oxide oxidation of pentacyclic bis-p-quinone derivative (3) stereo- and regioselectively. We also report a large-scale synthesis of cribrostatin 4 (renieramycin H) via the C3-C4 double bond formation in an early stage based on the Avendaño’s protocol, from readily available 1-acetyl-3-(3-methyl-2,4,5-trimethylphenyl)methyl-piperazine-2,5-dione (8) in 18 steps (8.3% overall yield). The synthesis provides unambiguous evidence supporting the original structure of renieramycin I. |
| Databáze: | OpenAIRE |
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