Expedient Synthesis of Alphitolic Acid and Its Naturally Occurring 2‑O‑Ester Derivatives
The expedient synthesis of alphitolic acid (1) as well as its natural C-3-epimer and 2-O-ester derivatives was accomplished in a few steps from the readily commercially available betulin (9). A Rubottom oxidation delivered an α-hydroxy group in a stereo- and chemoselective manner. The diastereoselec...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2019-04, Vol.82 (4), p.895-902 |
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| Sprache: | eng |
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| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 82 |
| creator | Park, Somin Cho, Jihee Jeon, Hongjun Sung, Sang Hyun Lee, Seunghee Kim, Sanghee |
| description | The expedient synthesis of alphitolic acid (1) as well as its natural C-3-epimer and 2-O-ester derivatives was accomplished in a few steps from the readily commercially available betulin (9). A Rubottom oxidation delivered an α-hydroxy group in a stereo- and chemoselective manner. The diastereoselective reduction of the α-hydroxy ketone was key to accessing the 1,2-diol moiety of this class of natural products. Our concise and stereoselective synthetic protocol allowed the gram-scale synthesis of these natural products, which will facilitate future biological evaluations. |
| doi_str_mv | 10.1021/acs.jnatprod.8b00986 |
| format | Article |
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| identifier | ISSN: 0163-3864 |
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| language | eng |
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| source | ACS Publications |
| title | Expedient Synthesis of Alphitolic Acid and Its Naturally Occurring 2‑O‑Ester Derivatives |
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