37172-97-7Relevant academic research and scientific papers
Synthesis of 4-acetylisocoumarin: First total syntheses of AGI-7 and sescandelin
Kim, Sanghee,Fan, Gao-Jun,Lee, Jaekwang,Lee, Jung Joon,Kim, Deukjoon
, p. 3127 - 3130 (2002)
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.
Synthesis and structural revision of phomopsin B, a novel polyketide carrying a 10-membered cyclic-ether ring
Izuchi, Yuko,Koshino, Hiroyuki,Hongo, Yayoi,Kanomata, Nobuhiro,Takahashi, Shunya
supporting information; experimental part, p. 3360 - 3363 (2011/08/22)
Total synthesis of the proposed structure 2 for phomopsin B was achieved by using an intramolecular olefin metathesis as a key step. The spectral data, however, did not match with those of the natural product reported. Re-examination of the reported NMR data led to the structural revision of phomopsin B to known dothiorelone A 18. The R configuration of dothiorelone A was determined by total synthesis through a cross-metathesis with a chiral olefin 19.
New DNA binding ligands as a model of chromomycin A3
Imoto, Shuhei,Haruta, Yoshinari,Watanabe, Kyouichi,Sasaki, Shigeki
, p. 4855 - 4859 (2007/10/03)
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
Synthesis of Siphulin, a Naturally Occurring Homoflavone
Kjaer, Anders,Kjaer, Dana
, p. 65 - 68 (2007/10/02)
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,
