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Total Synthesis of Hinckdentine A

Authors
Jeon, JiyeLee, Sang EunCheon, Cheol-Hong
Issue Date
19-3월-2021
Publisher
AMER CHEMICAL SOC
Citation
ORGANIC LETTERS, v.23, no.6, pp.2169 - 2173
Indexed
SCIE
SCOPUS
Journal Title
ORGANIC LETTERS
Volume
23
Number
6
Start Page
2169
End Page
2173
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/49349
DOI
10.1021/acs.orglett.1c00323
ISSN
1523-7060
Abstract
The total synthesis of (+/-)-hinckdentine A is described herein. A cyanide-catalyzed imino-Stetter reaction of the aldimine derived from ethyl 2-amino-3,5-dibromocinnamate and 5-bromo-2-nitrobenzaldehyde followed by oxidative rearrangement afforded a 2,2-disubstituted 3-indolinone derivative containing the carbon skeleton and all of the functional groups present in the natural product correctly positioned, including three bromine atoms. Subsequent D-ring formation and seven-membered C-ring construction completed the total synthesis of hinckdentine A.
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