ArticleBeilstein journal of organic chemistry2016
Study on the synthesis of the cyclopenta[f]indole core of raputindole A.
Article in Beilstein journal of organic chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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Who cites it
2 citing papers in PubMed, 12 citations in OpenAlex.
- Synthesis of (-)-Dihydroraputindole D by Enantioselective Benzoylation of a 1,3-Diol Intermediate.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Total Synthesis of (+)-Raputindole A: An Iridium-Catalyzed Cyclization Approach.Organic letters · 2020Article
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3 authors at 1 institution in 1 country.
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Abstract
The raputindoles from the rutaceous tree Raputia simulans share a cyclopenta[f]indole partial structure the synthesis of which is subject of this investigation. An efficient route to a series of 1,5-di(indol-6-yl)pentenones was developed via Mo/Au-catalyzed Meyer-Schuster rearrangement of tertiary propargylic alcohol precursors. However, none of the enones underwent the desired Nazarov cyclization to a cyclopenta[f]indole. More suitable were 6-hydroxyallylated indolines which gave good yields of cyclopenta[f]indolines after treatment with SnCl4, as soon as sterically demanding β-cyclocitral adducts were reacted. Most successful were Pt(II) and Au(I)-catalyzed cyclizations of N-TIPS-protected indolin-6-yl-substituted propargylacetates which provided the hydrogenated tricyclic cyclopenta[f]indole core system in high yield.
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