ArticleThe Journal of organic chemistry2018
Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Enantioselective Total Synthesis of (-)-Psiguadial A.Angewandte Chemie (International ed. in English) · 2025Article
- Creation of a Chiral All-Carbon Quaternary Center Induced by CFOrganic letters · 2024Article
- Visible Light-Mediated Dearomative Hydrogen Atom Abstraction/ Cyclization Cascade of Indoles.Angewandte Chemie (International ed. in English) · 2022Article
- Preparation and Synthetic Applications of Five-to-Seven-Membered Cyclic α-Diazo Monocarbonyl Compounds.Molecules (Basel, Switzerland) · 2022Review
- A Study of an 8-Aminoquinoline-Directed C(spThe Journal of organic chemistry · 2021Article
- An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study.Natural product reports · 2021Review
- Anti-Estrogenic Activity of Guajadial Fraction, from Guava Leaves (Molecules (Basel, Switzerland) · 2020Article
- Synthesis of Elaborate Benzofuran-2-carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C-H Arylation and Transamidation Chemistry.Molecules (Basel, Switzerland) · 2020Article
- Unraveling Plant Natural Chemical Diversity for Drug Discovery Purposes.Frontiers in pharmacology · 2020Review
- Recent advances in the synthesis of gem-dimethylcyclobutane natural products.Natural product reports · 2019Review
- Directed C(spChemical science · 2019Article
- Recent Advances in Enantioselective Photochemical Reactions of Stabilized Diazo Compounds.Molecules (Basel, Switzerland) · 2019Review
- A modular approach to prepare enantioenriched cyclobutanes: synthesis of (+)-rumphellaone A.Chemical science · 2019Article
- It's alive!Nature chemistry · 2018Article
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5 authors.
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Abstract
(+)-Psiguadial B is a diformyl phloroglucinol meroterpenoid that exhibits antiproliferative activity against the HepG2 human hepatoma cancer cell line. This full account details the evolution of a strategy that culminated in the first enantioselective total synthesis of (+)-psiguadial B. A key feature of the synthesis is the construction of the trans-cyclobutane motif by a Wolff rearrangement with in situ catalytic, asymmetric trapping of the ketene. An investigation of the substrate scope of this method to prepare enantioenriched 8-aminoquinolinamides is disclosed. Three routes toward (+)-psiguadial B were evaluated that featured the following key steps: (1) an ortho-quinone methide hetero-Diels-Alder cycloaddition to prepare the chroman framework, (2) a Prins cyclization to form the bridging bicyclo[4.3.1]decane system, and (3) a modified Norrish-Yang cyclization to generate the chroman. Ultimately, the successful strategy employed a ring-closing metathesis to form the seven-membered ring and an intramolecular O-arylation reaction to complete the polycyclic framework of the natural product.
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