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

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Title
Synthesis of 4-acetylisocoumarin: first total syntheses of AGI-7 and sescandelin
Author(s)
Sang Hee Kim; Gao Jun Fan; Jae Kwang Lee; Jung Joon Lee; Deuk Joon Kim
Bibliographic Citation
Journal of Organic Chemistry, vol. 67, no. 9, pp. 3127-3130
Publication Year
2002
Abstract
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.
ISSN
0022-3263
Publisher
Amer Chem Soc
DOI
http://dx.doi.org/10.1021/jo010789b
Type
Article
Appears in Collections:
1. Journal Articles > Journal Articles
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