Synthesis of 4-acetylisocoumarin: first total syntheses of AGI-7 and sescandelin.

@article{Kim2002SynthesisO4,
  title={Synthesis of 4-acetylisocoumarin: first total syntheses of AGI-7 and sescandelin.},
  author={Sanghee Kim and Gao-jun Fan and Jaekwang Lee and Jung Joon Lee and Deukjoon Kim},
  journal={The Journal of organic chemistry},
  year={2002},
  volume={67 9},
  pages={
          3127-30
        }
}
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… 
Synthesis of Isocoumarins via Silver(I)-Mediated Annulation of Enol Esters.
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Silver-mediated annulation of 2-iodo enol esters leading to 4- and 3,4-substituted isocoumarins was accomplished selectively at room temperature and, owing to the mildness of the current protocol, 4-acyl 3- substituting isocOUmarins were efficiently produced without any deacylation.
Furan ring opening — isocoumarine ring closure: A recyclization reaction of 2‐carboxyaryldifurylmethanes
A general method for the synthesis of isocoumarine derivatives has been developed. Bis(5-R-2-furyl)methylbenzoic acids (R = methyl, ethyl) underwent recyclization and subsequent cyclization into
Synthesis of 6,8-Dihydroxy-3-(2′-Acetyl-3′, 5′-Dihydroxyphenyl)Methylisocoumarin Related to Feralolide
  • A. Saeed
  • Chemistry
    Natural product research
  • 2004
TLDR
Base-catalyzed self-condensation of 3,5-dimethoxyhomophthalic acid directly furnished the 6,8-dihydroxy-3-(2′-acetyl-3′,5′- dihydroxyphenyl)methylisocoumarin related to the natural product feralolide.
Regioselective Synthesis of 4-(Arylsulfanyl)-2-hydroxyhomophthalates by [4+2] Cycloaddition of 3-(Arylsulfanyl)-1-(trimethylsilyloxy)buta-1,3-dienes with Dimethyl Penta-2,3-dienedioate
The [4+2] cycloaddition of 3-(arylsulfanyl)-1-(trimethylsilyloxy)buta-1,3-dienes with dimethyl penta-2,3-dienedioate provides a convenient and regioselective approach to a variety of
8-Hydro­xy-3,4-di­methyl­isocoumarin
The title compound, C11H10O2, known as oospolactone, is a simple isocoumarin which has been isolated as a secondary metabolite from a culture extract of the fungi Gloeophyl­lum subferrugineum and G.
Dimethyl 2,3‐Pentadienedioate
[1712-36-3] C7H8O4 (MW 156.15) InChI = 1S/C7H8O4/c1-10-6(8)4-3-5-7(9)11-2/h4-5H,1-2H3 InChIKey = FJLLBKDQCMPUSU-UHFFFAOYSA-N (reactive in Diels–Alder cycloadditions that
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References

Synthesis of 4-acetylisocoumarin: first total syntheses of AGI-7 and sescandelin.
TLDR
A practical synthetic route to 4-acetylisocoumarins and the first total synthesis of AGI-7 (5) and sescandelin (4) are described and the enantioselective reduction of AGi-7 by borane in the presence of Corey's (S)-oxazaborolidine reagent afforded (+)-sesc andelin with a 93% ee.