ArticleChemical science2020
Total synthesis and complete configurational assignment of amphirionin-2.
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 5 papers.
What it found
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Who cites it
5 citing papers in PubMed, 12 citations in OpenAlex.
- Cobalt catalysis in organic synthesis: a powerful tool in the synthesis of natural products and pharmaceutically active compounds.RSC advances · 2026Review
- Endophytic fungi as a potential source of anti-cancer drug.Archives of microbiology · 2024Review
- Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review.Molecules (Basel, Switzerland) · 2023Review
- Total Synthesis and Structural Assignment of (-)-Fusaequisin A.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural Products.Marine drugs · 2021Review
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Amphirionin-2 is a linear polyketide metabolite that exhibits potent and selective cytotoxic activity against certain human cancer cell lines. We disclose herein the first total synthesis of amphirionin-2 and determination of its absolute configuration. Our synthesis featured an extensive use of cobalt-catalyzed Mukaiyama-type cyclization of γ-hydroxy olefins for stereoselective formation of all the tetrahydrofuran rings found in the natural product, and a late-stage Stille-type coupling for convergent assembly of the entire carbon backbone. Four candidate diastereomers of amphirionin-2 were synthesized in a unified, convergent manner, and their spectroscopic/chromatographic properties were compared with those of the authentic material. The present study culminated in the reassignment of the C5/C7 relative configuration, assignment of the C12/C18 relative configuration, and determination of the absolute configuration of amphirionin-2.
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What OpenQuestion holds
Registered trials
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