ArticleChemical science2020
Total syntheses of spiroviolene and spirograterpene A: a structural reassignment with biosynthetic implications.
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
What it found
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Who cites it
6 citing papers in PubMed.
- Total Synthesis of (-)-Psathyrin A Enabled by Radical Cyclization.Journal of the American Chemical Society · 2025Article
- Total synthesis and target identification of marine cyclopiane diterpenes.Nature communications · 2024Article
- Confirmation of the stereochemistry of spiroviolene.Beilstein journal of organic chemistry · 2024Article
- Evolution towards green radical generation in total synthesis.Chemical Society reviews · 2021Review
- Engineering of Ancestors as a Tool to Elucidate Structure, Mechanism, and Specificity of Extant Terpene Cyclase.Journal of the American Chemical Society · 2021Article
- Revision of the Cyclisation Mechanism for the Diterpene Spiroviolene and Investigations of Its Mass Spectrometric Fragmentation.Chembiochem : a European journal of chemical biology · 2021Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
The recent natural product isolates spiroviolene and spirograterpene A are two relatively non-functionalized linear triquinane terpenes with a large number of structural homologies. Nevertheless, three significant areas of structural disparity exist based on their original assignments, one of which implies a key stereochemical divergence early in their respective biosyntheses. Herein, using two known bicyclic ketone intermediates, a core Pd-catalyzed Heck cyclization sequence, and several chemoselective transformations, we describe concise total syntheses of both natural product targets and propose that the structure of spiroviolene should be reassigned. As a result, these natural products possess greater homology than previously anticipated.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.