ArticleOrganic letters2012
Halocarbocyclization entry into the oxabicyclo[4.3.1]decyl exomethylene-δ-lactone cores of linearifolin and zaluzanin A: exploiting combinatorial catalysis.
Article in Organic letters, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed.
- Exploiting Archaeal/Thermostable Enzymes in Synthetic Chemistry: Back to the Future?ChemCatChem · 2024Article
- Biomacromolecule-Assisted Screening for Reaction Discovery and Catalyst Optimization.Chemical reviews · 2022Review
- Rapid Enantioselective and Diastereoconvergent Hybrid Organic/Biocatalytic Entry into the Oseltamivir Core.The Journal of organic chemistry · 2021Article
- A Hammett Study of Clostridium acetobutylicum Alcohol Dehydrogenase (CaADH): An Enzyme with Remarkable Substrate Promiscuity and Utility for Organic Synthesis.Synlett : accounts and rapid communications in synthetic organic chemistry · 2020Article
- The In Situ Enzymatic Screening (ISES) Approach to Reaction Discovery and Catalyst Identification.Current protocols in chemical biology · 2017Article
- A thiocyanopalladation/carbocyclization transformation identified through enzymatic screening: stereocontrolled tandem C-SCN and C-C bond formation.Chemical science · 2017Article
- Synthesis of Novel C-Pivot Lariat 18-Crown-6 Ethers and their Efficient Purification.Synlett : accounts and rapid communications in synthetic organic chemistry · 2015Article
- Mini-ISES identifies promising carbafructopyranose-based salens for asymmetric catalysis: Tuning ligand shape via the anomeric effect.Science advances · 2015Article
- Exploiting Enzymatic Dynamic Reductive Kinetic Resolution (DYRKR) in Stereocontrolled Synthesis.Advanced synthesis & catalysis · 2015Article
- Contemporary screening approaches to reaction discovery and development.Nature chemistry · 2014Review
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Abstract
A streamlined entry into the sesquiterpene lactone (SQL) cores of linearifolin and zaluzanin A is described. Stereochemistry is controlled through transformations uncovered by ISES (In Situ Enzymatic Screening). Absolute stereochemistry derives from kinetic resolution of 5-benzyloxypentene-1,2-oxide, utilizing a β-pinene-derived-Co(III)-salen. Relative stereochemistry (1,3-cis-fusion) is set via formal halometalation/carbocyclization, mediated by [Rh(O(2)CC(3)F(7))(2)](2)/LiBr. Subsequent ring-closing metathesis (RCM-Grubbs II) yields the title exomethylene-δ-lactone SQL cores. In complementary fashion, RCM with Grubbs-I catalyst provides the oxabicyclo[3.3.1]nonyl core of xerophilusin R and zinagrandinolide.
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