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1 article(s) from Kock, Mario

Study on the synthesis of the cyclopenta[f]indole core of raputindole A

Nils Marsch,
Mario Kock and
Thomas Lindel

Beilstein J. Org. Chem. 2016, 12, 334–342, doi:10.3762/bjoc.12.36

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Figure 1: Bisindole alkaloid raputindole A (1) from the Amazonian tree Raputia simulans.

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Scheme 1: Investigated synthetic precursors B–E of the cyclopenta[f]indole moiety (A) of raputindole A (1), a...

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Scheme 2: 6-Iodoindole (2) serves twice as starting material towards indole-6-yl-substituted enone 8, obtaine...

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Scheme 3: Assembly of 5-oxygenated bisindolylpentenones. DMB: 3,4-dimethoxybenzyl, DMFDMA: N,N-dimethylformal...

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Scheme 4: Benzylic oxidation as side reaction of DMB removal.

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Scheme 5: Hydroxyalkylation of N-protected indoles with β-cyclocitral and SnCl₄-induced cyclization.

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Scheme 6: Behavior of indolines after SnCl₄-induced generation of allyl cations.

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Scheme 7: Pt(II) and Au(I)-catalyzed cyclizations of propargylacetates 46 and 47 afforded cyclopenta[f]indoli...

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Published 23 Feb 2016

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