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…
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[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…
References
Synthesis of 4-acetylisocoumarin: first total syntheses of AGI-7 and sescandelin.
- ChemistryThe Journal of organic chemistry
- 2002
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.