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Title 

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

Authors 

Sang Hee KimGao Jun FanJae Kwang LeeJung Joon LeeDeuk Joon Kim

Publisher 

American Chemical Society

Issue Date 

2002

Citation 

Journal of Organic Chemistry, vol. 67, no. 9, pp. 3127-3130

Keywords 

synthesis (chemical)4 acetylisocoumarinagi 7sescandelindrug synthesis

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

Link 

http://dx.doi.org/10.1021/jo010789b

Appears in Collections

1. Journal Articles > Journal Articles

Registered Date

2017-04-19


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