ArticleNature chemistry2017
Iterative assembly line synthesis of polypropionates with full stereocontrol.
Article in Nature chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed.
- Strategic 1,n-migration of boronate complexes: a novel platform for remote C-C bond construction.Molecular diversity · 2026Review
- Atom-by-Atom Iterative Synthetic Logic: Laying the Foundation for Programmable Automated Construction of Small Organic Molecules.ACS central science · 2025Review
- Harnessing the β-boron effect for regioselective Ru-catalyzed hydrosilylation of internal alkynes.Nature communications · 2025Article
- Syntheses of Marine Natural Products via Matteson Homologations and Related Processes.Marine drugs · 2025Review
- Iterative Catalyst-Controlled Diastereoselective Matteson Homologations Enable the Selective Synthesis of Benzestrol Isomers.Journal of the American Chemical Society · 2024Article
- Mechanochemical Synthesis of α-halo Alkylboronic Esters.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Photogeneration of α-Bimetalloid Radicals via Selective Activation of Multifunctional C1 Units.Journal of the American Chemical Society · 2024Article
- Iterative SuFEx approach for sequence-regulated oligosulfates and its extension to periodic copolymers.Nature communications · 2024Article
- Ni-catalysed assembly of axially chiral alkenes from alkynyl tetracoordinate borons via 1,3-metallate shift.Nature chemistry · 2024Article
- Application of Chiral Transfer Reagents to Improve Stereoselectivity and Yields in the Synthesis of the Antituberculosis Drug Bedaquiline.Organic process research & development · 2023Article
- Diastereodivergent Catalysis.JACS Au · 2023Review
- Regioselective Electrophilic Addition to Propargylic B(MIDA)s Enabled by β-Boron Effect.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- A unified strategy for the synthesis of aldohexoses by boronate assisted assembly of CHChemical science · 2023Article
- Organogel delivery vehicles for the stabilization of organolithium reagents.Nature chemistry · 2023Article
- The Impact of Boron Hybridisation on Photocatalytic Processes.Angewandte Chemie (International ed. in English) · 2022Review
- Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes.Nature communications · 2022Article
- Stereocontrolled Total Synthesis of Bastimolide B Using Iterative Homologation of Boronic Esters.Journal of the American Chemical Society · 2022Article
- Article
- Cross-Electrophile Coupling of Unactivated Alkyl Chlorides.Journal of the American Chemical Society · 2020Article
- Ruthenium-catalysed multicomponent synthesis of the 1,3-dienyl-6-oxy polyketide motif.Nature chemistry · 2020Article
Corrections and comments
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The polypropionate motif is ubiquitous, being characteristic of the most important family of natural products for human health, the polyketides. Numerous strategies have been devised to construct these molecules with high stereocontrol, but certain stereoisomers remain challenging to prepare. We now describe the development of an iterative assembly line strategy for the construction of polypropionates. An assembly line strategy for the synthesis of deoxypolypropionates has already been described. However, the introduction of carbinol units required the development of new building blocks and new reaction conditions. This has been achieved by the use of enantioenriched lithiated α-chlorosilanes [1-((2'-lithiochloromethyldimethylsilyl)-methyl)-2-(methoxymethyl)-pyrrolidine], thus enabling the programmed synthesis of polypropionates in a fully stereocontrolled manner, including the stereochemically challenging anti-anti isomers. The versatility of the approach is exemplified in its extension to the synthesis of 1,3-related polyols. The methodology now allows access to a much wider family of polyketide natural products with stereochemistry being dialled in at will.
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Registered trials
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