ReviewNatural product reports2014
Polyketide construction via hydrohydroxyalkylation and related alcohol C-H functionalizations: reinventing the chemistry of carbonyl addition.
Review in Natural product reports, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 75 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
75 citing papers in PubMed, 166 citations in OpenAlex.
- Stereoselective Synthesis and Functionalization of Acetylenic Boronic Esters.Organic letters · 2026Article
- Enantioselective Carbonyl Crotylation of Alcohol Proelectrophiles via Ruthenium-Catalyzed Hydrogen Autotransfer: Innovation Inspired by Polyketide Total Synthesis.ACS catalysis · 2026Article
- Functionalisation of homopropargyl boronic estersRSC advances · 2026Article
- Total Synthesis ofJournal of the American Chemical Society · 2026Article
- Enantioselective Butadiene-Mediated Aldehyde Crotylation of Alcohol Proelectrophiles: RuHCl(CO)(PPhOrganic letters · 2026Article
- Formal Synthesis of Fostriecin via Asymmetric Alcohol-Mediated Carbonyl Allylation.Organic letters · 2025Article
- Catalytic Enantioselective C-C Coupling of Alcohols for Polyketide Total Synthesis beyond Chiral Auxiliaries and Premetalated Reagents.Chemical reviews · 2024Review
- Total Synthesis of the Phenylnaphthacenoid Type II Polyketide Antibiotic Formicamycin H via Regioselective Ruthenium-Catalyzed Hydrogen Auto-Transfer [4 + 2] Cycloaddition.Journal of the American Chemical Society · 2024Article
- Total Synthesis of the Allenic Macrolide (+)-Archangiumide.Journal of the American Chemical Society · 2024Article
- Enantioselective Transfer Hydrogenative Cycloaddition Unlocks the Total Synthesis of SF2446 B3: An Aglycone of Arenimycin and SF2446 Type II Polyketide Antibiotics.Journal of the American Chemical Society · 2023Article
- Synthetic Study of Natural Metabolites Containing a Benzo[International journal of molecular sciences · 2023Article
- Article
- Allyl Alcohol as an Acrolein Equivalent in Enantioselective C-C Coupling: Total Synthesis of Amphidinolides R, J, and S.Journal of the American Chemical Society · 2023Article
- Asymmetric Ruthenium-Catalyzed Carbonyl Allylations by Gaseous Allene via Hydrogen Auto-Transfer: 1° vs 2° Alcohol Dehydrogenation for Streamlined Polyketide Construction.ACS catalysis · 2023Article
- Benzyl Alcohol/Salicylaldehyde-Type Polyketide Metabolites of Fungi: Sources, Biosynthesis, Biological Activities, and Synthesis.Marine drugs · 2022Review
- Ruthenium-Catalyzed Butadiene-Mediated Crotylation and Oxazaborolidine-Catalyzed Vinylogous Mukaiyama Aldol Reaction for The Synthesis of C1-C19 and C23-C35 of Neaumycin B.Angewandte Chemie (International ed. in English) · 2022Article
- Stereo- and Site-Selective Crotylation of Alcohol Proelectrophiles via Ruthenium-Catalyzed Hydrogen Auto-Transfer Mediated by Methylallene and Butadiene.Angewandte Chemie (International ed. in English) · 2022Article
- Optimized Asymmetric Synthesis of Umuravumbolide.ACS omega · 2022Article
- Chiral Amines via Enantioselective π-Allyliridium-Accounts of chemical research · 2022Article
- Total Synthesis of Bipolamine I.Journal of the American Chemical Society · 2022Article
15 more citing papers are in PubMed but not listed here.
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Despite the longstanding importance of polyketide natural products in human medicine, nearly all commercial polyketide-based drugs are prepared through fermentation or semi-synthesis. The paucity of manufacturing routes involving de novo chemical synthesis reflects the inability of current methods to concisely address the preparation of these complex structures. Direct alcohol C-H bond functionalization via"C-C bond forming transfer hydrogenation" provides a powerful, new means of constructing type I polyketides that bypasses stoichiometric use of chiral auxiliaries, premetallated C-nucleophiles, and discrete alcohol-to-aldehyde redox reactions. Using this emergent technology, total syntheses of 6-deoxyerythronolide B, bryostatin 7, trienomycins A and F, cyanolide A, roxaticin, and formal syntheses of rifamycin S and scytophycin C, were accomplished. These syntheses represent the most concise routes reported to any member of the respective natural product families.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.