11-Step Total Synthesis of Araiosamines
A concise route to a small family of exotic marine alkaloids known as the araiosamines has been developed, and their absolute configuration has been assigned. The dense array of functionality, high polarity, and rich stereochemistry coupled with equilibrating topologies present an unusual challenge...
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| Veröffentlicht in: | Journal of the American Chemical Society 2016-11, Vol.138 (43), p.14234-14237 |
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| container_end_page | 14237 |
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| container_issue | 43 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 138 |
| creator | Tian, Maoqun Yan, Ming Baran, Phil S |
| description | A concise route to a small family of exotic marine alkaloids known as the araiosamines has been developed, and their absolute configuration has been assigned. The dense array of functionality, high polarity, and rich stereochemistry coupled with equilibrating topologies present an unusual challenge for chemical synthesis and an opportunity for innovation. Key steps involve the use of a new reagent for guanidine installation, a remarkably selective C–H functionalization, and a surprisingly simple final step that intersects a presumed biosynthetic intermediate. Synthetic araiosamines were shown to exhibit potency against Gram-positive and -negative bacteria despite a contrary report of no activity. |
| doi_str_mv | 10.1021/jacs.6b09701 |
| format | Article |
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| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 2016-11, Vol.138 (43), p.14234-14237 |
| issn | 0002-7863 1520-5126 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Amines - chemical synthesis Amines - chemistry Amines - pharmacology Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Cell Line, Tumor Chemistry Techniques, Synthetic Communication Escherichia coli - drug effects Guanidine - chemistry Humans Staphylococcus aureus - drug effects Stereoisomerism |
| title | 11-Step Total Synthesis of Araiosamines |
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