Synthesis of N-Protected Staurosporinones

Autor:	Hideo Nagasaki, Yasuhiro Wada, Masao Tokuda, Kazuhiko Orito
Rok vydání:	2007
Předmět:	Indoles Intramolecular reaction Nitrile Carbazole Organic Chemistry Carbazoles Ketones Staurosporine Anisole Medicinal chemistry Chemical synthesis Catalysis Indole Alkaloids chemistry.chemical_compound chemistry 2 3-Dichloro-5 6-dicyano-1 4-benzoquinone Organic chemistry Methiodide Carbonylation
Zdroj:	The Journal of Organic Chemistry. 72:2008-2014
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo062184r
Popis:	We report a method for the synthesis of N-protected staurosporinones, which are useful for the synthesis of indolo[2,3-a]pyrrolo[3,4-c]carbazole alkaloids and related compounds. An interaction of gramine methiodide (2) with 3-(N-benzyl)indolylacetonitrile (3) in the presence of t-BuLi, followed by a CF3COOH-catalyzed intramolecular indole-indole coupling and dehydrogenation with DDQ, produced 5-cyanoindolo[2,3-a]carbazole 6 almost quantitatively. Reduction of its cyano group followed by N-benzylation produced N-benzylaminomethylindolo[2,3-a]carbazole 8b, which was subjected to Pd(OAc)2-catalyzed direct aromatic carbonylation to give N-protected staurosporinone 9b. Treatment with AlCl3 in anisole removed N-benzyl groups to afford staurosporinone quantitatively.
Databáze:	OpenAIRE
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