ArticleJournal of the American Chemical Society2024
Total Synthesis of the Norcembranoid Scabrolide B and Its Transformation into Sinuscalide C, Ineleganolide, and Horiolide.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Asymmetric Total Synthesis of (+)-Ineleganolide.Angewandte Chemie (International ed. in English) · 2026Article
- Total Synthesis of Benthol A: Evidence for a Structure Revision.Journal of the American Chemical Society · 2026Article
- Total Synthesis of Benthol A: The Nominal and the Actual Natural Product.Journal of the American Chemical Society · 2026Article
- Marine natural products.Natural product reports · 2026Review
- Short, Enantioselective Total Synthesis of (+)-Ineleganolide.Journal of the American Chemical Society · 2025Article
- Collective Total Synthesis of a Unique Class of Liverworts-Derived Cembrane Diterpenoids.Angewandte Chemie (International ed. in English) · 2025Article
- Synthesis of Cyclobutane-Containing Tricyclic β-Lactams Based on a Saturated Scaffold Enabled by Iron-catalysed [2 + 2]-Cycloaddition.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
It was recognized only recently that the sister norcembranoids scabrolides A and B have notably different carbotricyclic scaffolds. Therefore, our synthesis route leading to scabrolide A could not be extended to its sibling. Rather, a conceptually new approach had to be devised that relied on a challenging intramolecular alkenylation of a ketone to forge the congested central cycloheptene ring at the bridgehead enone site; the required cyclization precursor was attained by a lanthanide-catalyzed Mukaiyama-Michael addition. The dissonant 1,4-oxygenation pattern was then installed by allylic rearrangement/oxidation of the enone, followed by suprafacial 1,3-transposition. Synthetic scabrolide B was transformed into sinuscalide C by dehydration and into ineleganolide by base-mediated isomerization/oxa-Michael addition, which has potential biosynthetic implications; under basic conditions, the latter compound converts into horiolide by an intricate biomimetic cascade.
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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.