ArticleJournal of the American Chemical Society2014
Enantioselective synthesis of (-)-maoecrystal V by enantiodetermining C-H functionalization.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Enantioselective C-H functionalization: logic and applications in the total synthesis of natural products.Chemical science · 2026Review
- Ligand-controlled divergent asymmetric C(spNature communications · 2025Article
- Dearomative logic in natural product total synthesis.Natural product reports · 2022Review
- "Sandwich" Diimine-Copper Catalysts for C-H Functionalization by Carbene Insertion.Angewandte Chemie (International ed. in English) · 2022Article
- Harnessing Natural Products by a Pharmacophore-Oriented Semisynthesis Approach for the Discovery of Potential Anti-SARS-CoV-2 Agents.Angewandte Chemie (International ed. in English) · 2022Article
- Asymmetric Total Synthesis of (-)-Phaeocaulisin A.Journal of the American Chemical Society · 2022Article
- Development of an enolate alkynylation approach towards the synthesis of the taiwanschirin natural products.Chemical science · 2021Article
- Enantioselective synthesis of highly oxygenated acyclic quaternary center-containing building blocksChemical science · 2020Article
- Scalable synthesis enabling multilevel bio-evaluations of natural products for discovery of lead compounds.Nature communications · 2018Article
- Synthesis of azasilacyclopentenes and silanolsChemical science · 2017Article
- Synthesis of Functionalized Dihydrobenzofurans by Direct Aryl C-O Bond Formation under Mild Conditions.Angewandte Chemie (International ed. in English) · 2016Article
- 11-Step Total Synthesis of (-)-Maoecrystal V.Journal of the American Chemical Society · 2016Article
- Generation of the Methoxycarbonyl Radical by Visible-Light Photoredox Catalysis and Its Conjugate Addition with Electron-Deficient Olefins.Organic letters · 2016Article
- Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms.Angewandte Chemie (International ed. in English) · 2016Review
- The synthesis of functionalized bridged polycycles via C-H bond insertion.Beilstein journal of organic chemistry · 2016Review
- Enantioselective carbenoid insertion into C(sp(3))-H bonds.Beilstein journal of organic chemistry · 2016Review
- 10-Step Asymmetric Total Synthesis and Stereochemical Elucidation of (+)-Dragmacidin D.Angewandte Chemie (International ed. in English) · 2015Article
- The daphniphyllum alkaloids: total synthesis of (-)-calyciphylline N.Journal of the American Chemical Society · 2015Article
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7 authors.
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Abstract
The evolution of a program directed at the enantioselective total synthesis of maoecrystal V, a highly modified ent-kauranoid, is described. An early stage chiral auxiliary-directed asymmetric C-H functionalization for the construction of a key benzofuran intermediate enabled the first asymmetric synthesis of the natural enantiomer of maoecrystal V, confirming the assigned stereochemistry. A divergent course of the central intramolecular Diels-Alder reaction, which is dependent on the nature of the dienophile, initially led to the development of an unanticipated and previously unknown isomer of maoecrystal V, which we named maoecrystal ZG. In light of the reported selective and potent cytotoxic activity of maoecrystal V, the cytotoxic properties of maoecrystal ZG were also investigated.
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