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Efficient Formal Synthesis of the Human Telomerase Inhibitor (±)-γ-Rubromycin
Balancing act: The correct balance of electronic factors in the naphthazarin and isocoumarin fragments facilitates the acid‐mediated spiroketalization step to afford the key densely functionalized spiroketal (see picture; EOM=ethoxymethyl) in the formal synthesis of (±)‐γ‐rubromycin. A novel regiose...
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| Published in: | Angewandte Chemie (International ed.) 2009-10, Vol.48 (43), p.7996-8000 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c4706-206fd12204433fe653a45b815a6979985bac4f1e78fc3724c203a9b4b780730b3 |
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| cites | cdi_FETCH-LOGICAL-c4706-206fd12204433fe653a45b815a6979985bac4f1e78fc3724c203a9b4b780730b3 |
| container_end_page | 8000 |
| container_issue | 43 |
| container_start_page | 7996 |
| container_title | Angewandte Chemie (International ed.) |
| container_volume | 48 |
| creator | Rathwell, Dominea C.K Yang, Sung-Hyun Tsang, Kit Y Brimble, Margaret A |
| description | Balancing act: The correct balance of electronic factors in the naphthazarin and isocoumarin fragments facilitates the acid‐mediated spiroketalization step to afford the key densely functionalized spiroketal (see picture; EOM=ethoxymethyl) in the formal synthesis of (±)‐γ‐rubromycin. A novel regioselective allyloxylation/Claisen rearrangement of 2‐azido‐1,4‐naphthoquinone provides access to the highly oxygenated naphthazarin fragment. |
| doi_str_mv | 10.1002/anie.200903316 |
| format | article |
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EOM=ethoxymethyl) in the formal synthesis of (±)‐γ‐rubromycin. 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| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie (International ed.), 2009-10, Vol.48 (43), p.7996-8000 |
| issn | 1433-7851 1521-3773 |
| language | eng |
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| source | Wiley |
| subjects | Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry antibiotics azides Benzene Derivatives - chemistry Crystallography, X-Ray Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Humans Isocoumarins - chemistry Molecular Conformation Naphthoquinones - chemistry natural product synthesis Quinones - chemical synthesis Quinones - chemistry spiroketals Telomerase - antagonists & inhibitors Telomerase - metabolism total synthesis |
| title | Efficient Formal Synthesis of the Human Telomerase Inhibitor (±)-γ-Rubromycin |
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