- New DNA binding ligands as a model of chromomycin A3
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Small molecules with DNA-binding affinity within the minor groove have become of great interest. In this study, new DNA-binding ligands were designed to mimic Chromomycin A3 (CRA3), which contains a hydroxylated tetrahydroanthracene
- Imoto, Shuhei,Haruta, Yoshinari,Watanabe, Kyouichi,Sasaki, Shigeki
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p. 4855 - 4859
(2007/10/03)
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- Synthesis of 4-acetylisocoumarin: First total syntheses of AGI-7 and sescandelin
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A practical synthetic route to 4-acetylisocoumarins and the first total synthesis of AGI-7 (5) and sescandelin (4) are described. The readily available homophthalate 8 was transformed to the vinylogous amide ester 13 in high overall yield. Upon treatment of 13 with refluxing aqueous formic acid, the desired 4-acetylisocoumarin (5) and its regioisomer 3-methyl-4-formylisocoumarin (17) were produced in a 3:1 ratio. After separation of the desired product (5) from the unwanted minor isomer, the enantioselective reduction of AGI-7 by borane in the presence of Corey's (S)-oxazaborolidine reagent afforded (+)-sescandelin (4) with a 93% ee.
- Kim, Sanghee,Fan, Gao-Jun,Lee, Jaekwang,Lee, Jung Joon,Kim, Deukjoon
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p. 3127 - 3130
(2007/10/03)
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- Synthesis of Siphulin, a Naturally Occurring Homoflavone
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Siphulin, the only homoflavone known in Nature, is synthesized from 2-hydroxy-4-benzyloxy-6-heptylacetophenone and methyl 2-carboxy-3,5-dibenzyloxyhomophthalate, reacting, in the presence of sodium hydride, to give tri-O-benzylprotosiphulin, convertible,
- Kjaer, Anders,Kjaer, Dana
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