Tandem Gold-Catalyzed Dehydrative Cyclization/Diels–Alder Reactions: Facile Access to Indolocarbazole Alkaloids

A gold-catalyzed synthesis of cyclic 2-oxodienes from readily prepared propargyl alcohols and the subsequent Diels–Alder reaction are reported. The dehydrative cyclization reactions proceeded smoothly, and the dienes formed in situ were demonstrated to undergo cycloaddition with a variety of dienoph...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 7; pp. 1754 - 1757
Main Authors Borrero, Nicholas V, DeRatt, Lindsey G, Ferreira Barbosa, Lais, Abboud, Khalil A, Aponick, Aaron
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.04.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
NEUROTROPHIC FACTOR
INDUCED NEURONAL DIFFERENTIATION
H BOND AMINATION
INHIBITORS
PC12 CELLS
TRIPHENYLPHOSPHINE
REDUCTIVE CYCLIZATION
EFFICIENT
INDOCARBAZOSTATIN-B
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Summary:A gold-catalyzed synthesis of cyclic 2-oxodienes from readily prepared propargyl alcohols and the subsequent Diels–Alder reaction are reported. The dehydrative cyclization reactions proceeded smoothly, and the dienes formed in situ were demonstrated to undergo cycloaddition with a variety of dienophiles. This method offers a new strategy for the synthesis of indolocarbazole alkaloids, whereby the convergent synthetic design allows for differentiation between the indole nitrogens.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00528