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2 article(s) from Marsch, Nils

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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SmI₂-mediated dimerization of indolylbutenones and synthesis of the myxobacterial natural product indiacen B

Nils Marsch,
Peter G. Jones and
Thomas Lindel

Beilstein J. Org. Chem. 2015, 11, 1700–1706, doi:10.3762/bjoc.11.184

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Figure 1: Prenylated indole alkaloids raputindole A from the rutaceous tree Raputia simulans and indiacen B f...

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Scheme 1: Synthesis and SmI₂-mediated reductive dimerization of natural product 5.

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Scheme 2: Model visualizing the stereochemical course of the cyclopentanol formation leading to product 6. Po...

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Scheme 3: Meyer–Schuster rearrangement of 13 and SmI₂-mediated reductive [3 + 2] cycloaddition, followed by e...

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Scheme 4: Nazarov-type cyclization of 14 to cyclopentanones 17 and 18; synthesis of verticillatine B (20).

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Scheme 5: Synthesis and X-ray analysis of indiacen B (2, ORTEP drawing with ellipsoides at 50% probability).

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Published 21 Sep 2015

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

SmI2-mediated dimerization of indolylbutenones and synthesis of the myxobacterial natural product indiacen B

SmI₂-mediated dimerization of indolylbutenones and synthesis of the myxobacterial natural product indiacen B