ArticleChemical science2017
Bioinspired synthesis of pentacyclic onocerane triterpenoids.
Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Palladium-catalyzed cross-coupling of alcohols with olefins by positional tuning of a counteranion.Science (New York, N.Y.) · 2024Article
- Discovery of fungal onoceroid triterpenoids through domainless enzyme-targeted global genome mining.Nature communications · 2024Article
- Analysis of vitamin D receptor binding affinities of enzymatically synthesized triterpenes including ambrein and unnatural onoceroids.Scientific reports · 2024Article
- Biogenetic space-guided synthesis of rearranged terpenoids.Chemical communications (Cambridge, England) · 2023Review
- Towards a comprehensive understanding of the structural dynamics of a bacterial diterpene synthase during catalysis.Nature communications · 2018Article
Corrections and comments
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Authors and funding
7 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The first chemical synthesis of pentacyclic onocerane triterpenoids has been achieved. A putative biomimetic tricyclization cascade is employed to forge a fused decalin-/oxepane ring system. The synthetic route proceeds to (+)-cupacinoxepin in seven steps and to (+)-onoceranoxide in eight steps in the longest linear sequence, when starting from geranyl chloride and (+)-sclareolide. The bioinspired epoxypolyene cyclization is supported by computational and enzymatic studies.
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Registered trials
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