| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5177361 | Phytochemistry Letters | 2012 | 4 Pages |
Abstract
When treated with (diethylamino)sulfur trifluoride (DAST), 11α-hydroxygedunin gave 11β-fluorogedunin and 9,11-didehydrogedunin, whereas deacetylgedunin afforded two skeletal rearranged products 6 and 7, in which the Me-30 had shifted from position 8 to position 7. Of those products, 11β-fluorogedunin and 6 were shown to be more cytotoxic than gedunin on P-388 leukemia cells.
Graphical abstractDownload full-size imageHighlights⺠A fluorinated gedunin derivative was prepared from 11α-hydroxygedunin. ⺠A skeletal rearrangement reaction occurred when deacetylgedunin was treated with DAST. ⺠The structure of the rearranged product was established by X-ray crystallography. ⺠Some analogs were found to be more cytotoxic than gedunin.
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Authors
Yukio Hitotsuyanagi, Kumiko Mitsui, Haruhiko Fukaya, Koichi Takeya,