ArticleThe Journal of organic chemistry2018
Six Trikentrin-like Cyclopentanoindoles from Trikentrion flabelliforme. Absolute Structural Assignment by NMR and ECD.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Molecular rearrangements as powerful tools in diversity-oriented natural products synthesis: a review.RSC advances · 2026Review
- TiClSynlett : accounts and rapid communications in synthetic organic chemistry · 2026Article
- Marine Natural Products from Flora and Fauna of the Western Australian Coast: Taxonomy, Isolation and Biological Activity.Molecules (Basel, Switzerland) · 2023Review
- Marine Indole Alkaloids-Isolation, Structure and Bioactivities.Marine drugs · 2021Review
- Synthesis of (-)-Dihydroraputindole D by Enantioselective Benzoylation of a 1,3-Diol Intermediate.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Synthesis of the tricyclic indole alkaloids, dilemmaones A and B.Tetrahedron · 2019Article
- Synergistic Anti-Marine drugs · 2019Article
- 6-Bromoindole Derivatives from the Icelandic Marine SpongeMarine drugs · 2018Article
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2 authors.
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Abstract
Six new cyclopenta[g]indoles were isolated from a West Australian sponge, Trikentrion flabelliforme Hentschel, 1912, and their structures elucidated by integrated spectroscopic analysis. The compounds are analogues of previously described trikentrins, herbindoles, and trikentramides from related Axinellid sponges. The assignment of absolute configuration of the new compounds was carried out largely by comparative analysis of specific rotation, calculated and measured ECD, and exploiting van't Hoff's principle of optical superposition. Five of the new compounds were chemically interconverted to establish their stereochemical relationships, leading to a simple chiroptical mnemonic for assignment of the this family of chiral indoles. The first biosynthetic hypothesis is advanced to explain the origin of the trikentrin-herbinole family and proposes a pyrrole-carboxylic thioester-initiated polyketide synthase mechanism.
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