ArticleAngewandte Chemie (International ed. in English)2016
Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (-)-Clavosolide A.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Environmentally Friendly Synthesis of Polysubstituted Pyrroles in Ionic Liquid via Gold-Catalyzed Propargylic Substitution/Hydration/Amination/Cycloisomerization Sequence.Molecules (Basel, Switzerland) · 2026Article
- Stereoselective Copper-Catalyzed Cross-Coupling of α-CFThe Journal of organic chemistry · 2025Article
- Syntheses of Marine Natural Products via Matteson Homologations and Related Processes.Marine drugs · 2025Review
- Synthetic efforts on the road to marine natural products bearing 4-RSC advances · 2021Review
- An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies.Molecules (Basel, Switzerland) · 2019Review
- Total Synthesis of Clavosolide A via Asymmetric Alcohol-Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction.Angewandte Chemie (International ed. in English) · 2019Article
- Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki-Miyaura cross-coupling.Chemical science · 2017Article
- Stereocontrolled Total Synthesis of (-)-Stemaphylline.Angewandte Chemie (International ed. in English) · 2017Article
- Short Enantioselective Total Synthesis of Tatanan A and 3-epi-Tatanan A Using Assembly-Line Synthesis.Angewandte Chemie (International ed. in English) · 2016Article
- Discovery, Total Synthesis and Key Structural Elements for the Immunosuppressive Activity of Cocosolide, a Symmetrical Glycosylated Macrolide Dimer from Marine Cyanobacteria.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.Journal of the American Chemical Society · 2016Article
- Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (-)-Clavosolide A.Angewandte Chemie (International ed. in English) · 2016Article
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4 authors.
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Abstract
Tetrahydropyrans are common motifs in natural products and have now been constructed with high stereocontrol through a three-component allylboration-Prins reaction sequence. This methodology has been applied to a concise (13 steps) and efficient (14 % overall yield) synthesis of the macrolide (-)-clavosolide A. The synthesis also features an early stage glycosidation reaction to introduce the xylose moiety and a lithiation-borylation reaction to attach the cyclopropyl-containing side chain.
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