ArticleNature communications2021
Unified divergent strategy towards the total synthesis of the three sub-classes of hasubanan alkaloids.
Article in Nature communications, 2021. 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.
- Total syntheses of (+)-dalesconols A and B enabled by triple-relayed remote chirality transfer.Nature communications · 2026Article
- Divergent Enantioselective Total Synthesis of (-)-Ajmalicine, (+)-Mayumbine, and (-)-Roxburghine C.Organic letters · 2025Article
- Transformation of the cyclohexane ring to the cyclopentane fragment of biologically active compounds.Beilstein journal of organic chemistry · 2025Review
- Natural Product Synthesis: The Endless Quest for Unreachable Perfection.ACS organic & inorganic Au · 2023Review
- Total Syntheses of (+)-Waixenicin A, (+)-9-Deacetoxy-14,15-deepoxyxeniculin, and (-)-Xeniafaraunol A.Journal of the American Chemical Society · 2023Article
- Article
- Late-Stage Diversification: A Motivating Force in Organic Synthesis.Journal of the American Chemical Society · 2021Article
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3 authors.
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Abstract
Elegant asymmetric synthesis of hasubanan alkaloids have been developed over the past decades. However, a divergent approach leading to all three sub-classes of this family of natural products remains unknown. We report herein the realization of such an endeavor by accomplishing enantioselective total syntheses of four representative members. The synthesis is characterized by catalytic enantioselective construction of the tricyclic compounds from which three different intramolecular C-N bond forming processes leading to three topologically different hasubanan alkaloids are developed. An aza-Michael addition is used for the construction of the aza-[4.4.3]-propellane structure of (-)-cepharamine, whereas an oxidation/double deprotection/intramolecular hemiaminal forming sequence is developed to forge the bridged 6/6/6/6 tetracycle of (-)-cepharatines A and C and a domino bromination/double deprotection/cyclization sequence allows the build-up of the 6/6/5/5 fused tetracyclic structure of (-)-sinoracutine.
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