ArticleNature communications2021
Biomimetic approach to the catalytic enantioselective synthesis of tetracyclic isochroman.
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 9 papers.
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Who cites it
9 citing papers in PubMed.
- Biosynthesis of O-Prenylated Chaetophenols Triggers Nonenzymatic Pathways toward Structural Diversity.Organic letters · 2026Article
- Ring contraction and ring expansion reactions in terpenoid biosynthesis and their application to total synthesis.Beilstein journal of organic chemistry · 2026Review
- Mechanistic studies on a biomimetic cycloaddition between phloroglucinol and 2-hydroxyethyl-α,β-unsaturated ketone.Journal of molecular modeling · 2025Article
- Article
- Recent advancements in the chemistry of Diels-Alder reaction for total synthesis of natural products: a comprehensive review (2020-2023).RSC advances · 2025Review
- Knoevenagel-IMHDA and -IMSDA sequences for the synthesis of chiral condensed O,N-, S,N- and N-heterocycles.RSC advances · 2025Article
- Diastereo-divergent synthesis of chiral hindered ethers via a synergistic calcium(II)/gold(I) catalyzed cascade hydration/1,4-addition reaction.Nature communications · 2024Article
- Catalytic asymmetric oxa-Diels-Alder reaction of acroleins with simple alkenes.Nature communications · 2023Article
- Selective radical cascade (4+2) annulation with olefins towards the synthesis of chroman derivativesChemical science · 2022Article
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Authors and funding
6 authors.
Funding
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Abstract
Polyketide oligomers containing the structure of tetracyclic isochroman comprise a large class of natural products with diverse activity. However, a general and stereoselective method towards the rapid construction of this structure remains challenging due to the inherent instability and complex stereochemistry of polyketide. By mimicking the biosynthetic pathway of this structurally diverse set of natural products, we herein develop an asymmetric hetero-Diels-Alder reaction of in-situ generated isochromene and ortho-quinonemethide. A broad range of tetracyclic isochroman frameworks are prepared in good yields and excellent stereoinduction (up to 95% ee) from readily available α-propargyl benzyl alcohols and 2-(hydroxylmethyl) phenols under mild conditions. This direct enantioselective cascade reaction is achieved by a Au(I)/chiral Sc(III) bimetallic catalytic system. Experimental studies indicate that the key hetero-Diels-Alder reaction involves a stepwise pathway, and the steric hindrance between in-situ generated isochromene and t-Bu group of Sc(III)/N,N'-dioxide complex is responsible for the enantioselectivity in the hetero-Diels-Alder reaction step.
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