ArticleJournal of the American Chemical Society2013
Total synthesis of (+)-trienomycins A and F via C-C bond-forming hydrogenation and transfer hydrogenation.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Enantioselective Carbonyl Crotylation of Alcohol Proelectrophiles via Ruthenium-Catalyzed Hydrogen Autotransfer: Innovation Inspired by Polyketide Total Synthesis.ACS catalysis · 2026Article
- Stereochemical Reassignment by Total Synthesis of an Ocular Pyridinium Bisretinoid of Retinal Pigment Epithelium Lipofuscin:Organic letters · 2025Article
- Catalytic Enantioselective C-C Coupling of Alcohols for Polyketide Total Synthesis beyond Chiral Auxiliaries and Premetalated Reagents.Chemical reviews · 2024Review
- Article
- Historical perspective on ruthenium-catalyzed hydrogen transfer and survey of enantioselective hydrogen auto-transfer processes for the conversion of lower alcohols to higher alcohols.Chemical science · 2022Review
- Enantioselective Metal-Catalyzed Reductive Coupling of Alkynes with Carbonyl Compounds and Imines: Convergent Construction of Allylic Alcohols and Amines.ACS catalysis · 2022Article
- Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.Angewandte Chemie (International ed. in English) · 2019Review
- New Ansamycins from the Deep-Sea-Derived BacteriumMarine drugs · 2018Article
- Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.Chemical reviews · 2018Review
- Synthesis of the C(1)-C(13) Fragment of Leiodermatolide via Hydrogen-Mediated C-C Bond Formation.Organic letters · 2017Article
- Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.Tetrahedron · 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
- Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.Topics in current chemistry · 2016Review
- Direct Generation of Triketide Stereopolyads via Merged Redox-Construction Events: Total Synthesis of (+)-Zincophorin Methyl Ester.Journal of the American Chemical Society · 2015Article
- Catalytic enantioselective C-H functionalization of alcohols by redox-triggered carbonyl addition: borrowing hydrogen, returning carbon.Angewandte Chemie (International ed. in English) · 2014Review
- Polyketide construction via hydrohydroxyalkylation and related alcohol C-H functionalizations: reinventing the chemistry of carbonyl addition.Natural product reports · 2014Review
- Asymmetric alcohol C-H allylation and syn-crotylation: C9-C20 of tetrafibricin.Organic letters · 2014Article
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Authors and funding
2 authors.
Funding
Abstract
The triene-containing C17-benzene ansamycins trienomycins A and F were prepared in 16 steps (longest linear sequence, LLS) and 28 total steps. The C11-C13 stereotriad was generated via enantioselective Ru-catalyzed alcohol CH syn crotylation followed by chelation-controlled carbonyl dienylation. Enantioselective Rh-catalyzed acetylene-aldehyde reductive coupling mediated by gaseous H2 was used to form a diene that ultimately was subjected to diene-diene ring closing metathesis to form the macrocycle. The present approach is 14 steps shorter (LLS) than the prior syntheses of trienomycins A and F, and 8 steps shorter than any prior synthesis of a triene-containing C17-benzene ansamycin.
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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.