A tandem gold(I)-catalyzed rearrangement/Nazarov reaction of enynyl acetates which efficiently provides cyclopenta[b]indol-1-ones as useful precursors for the synthesis of natural and bioactive compounds, is described. The synthetic potential of the methodology is demonstrated by the first total synthesis of bruceolline H.
Construction of Cyclopenta[b]indol-1-ones by a Tandem Gold(I)-Catalyzed Rearrangement/Nazarov Reaction and Application to the Synthesis of Bruceolline H / Scarpi, Dina; Petrović, Martina; Fiser, Béla; Gómez-Bengoa, Enrique; Occhiato, Ernesto G.. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 18:(2016), pp. 3922-3925. [10.1021/acs.orglett.6b01990]
Construction of Cyclopenta[b]indol-1-ones by a Tandem Gold(I)-Catalyzed Rearrangement/Nazarov Reaction and Application to the Synthesis of Bruceolline H
SCARPI, DINA;PETROVIC, MARTINA;OCCHIATO, ERNESTO GIOVANNI
2016
Abstract
A tandem gold(I)-catalyzed rearrangement/Nazarov reaction of enynyl acetates which efficiently provides cyclopenta[b]indol-1-ones as useful precursors for the synthesis of natural and bioactive compounds, is described. The synthetic potential of the methodology is demonstrated by the first total synthesis of bruceolline H.
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