Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis |
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Authors: | M.-Lluï sa Bennasar,Ester Zulaica,Daniel Solé ,Sandra Alonso |
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Affiliation: | Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Barcelona 08028, Spain |
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Abstract: | The azocino[4,3-b]indole system, tricyclic substructure of the indole alkaloids apparicine and ervaticine, is efficiently assembled by ring-closing metathesis of 2-allyl-3-(allylaminomethyl)indoles. The metathesis sites are introduced into the indole nucleus by reductive amination of a 3-formyl derivative with allylamine, followed by α-lithiation with subsequent electrophilic trapping with acrolein. |
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Keywords: | Ring-closing metathesis Indole Indole alkaloids |
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