Gold-Catalyzed Selective 6-exo-dig and 7-endo-dig Cyclizations of Alkyn-Tethered Indoles To Prepare Rutaecarpine Derivatives

An efficient method to synthesize rutaecarpine derivatives via the gold-catalyzed selective cyclization of alkyn-tethered indoles under mild conditions is described. The alkyn-tethered indole can undergo 6-exo-dig cyclization by oxidation and sequential gold catalysis, while it goes through 7-endo-d...

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Published inJournal of organic chemistry Vol. 83; no. 4; pp. 2006 - 2017
Main Authors Kong, Xiang-Fei, Zhan, Feng, He, Guo-Xue, Pan, Cheng-Xue, Gu, Chen-Xi, Lu, Ke, Mo, Dong-Liang, Su, Gui-Fa
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.02.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REARRANGEMENT
APOPTOSIS
CELLS
HETEROCYCLES
GOLD(I)-CATALYZED CYCLIZATION
EVODIAMINE
PROGRESS
QUINAZOLINE ALKALOIDS
CASCADE
LUOTONIN-A
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Summary:An efficient method to synthesize rutaecarpine derivatives via the gold-catalyzed selective cyclization of alkyn-tethered indoles under mild conditions is described. The alkyn-tethered indole can undergo 6-exo-dig cyclization by oxidation and sequential gold catalysis, while it goes through 7-endo-dig cyclization by gold catalysis and sequential oxidation. Substrate scope studies reveal that the selectivity of cyclization was controlled by the substrates with sp3 and sp2 hybridization of carbon at the 2 position in quinazolinone. Furthermore, the rutaecarpine scaffold was prepared in 67% yield at gram scale easily in four steps from isatoic anhydride.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02956