ArticleJournal of the American Chemical Society2016
Syntheses of (+)-30-epi-, (-)-6-epi-, (±)-6,30-epi-13,14-Didehydroxyisogarcinol and (±)-6,30-epi-Garcimultiflorone A Utilizing Highly Diastereoselective, Lewis Acid-Controlled Cyclizations.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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6 citing papers in PubMed.
- NiH-Catalyzed Enantioconvergent α-Alkenylation of Carbonyl Compounds via Markovnikov Alkyne Hydronickellation.Angewandte Chemie (International ed. in English) · 2026Article
- Synthesis and Multiplexed Activity Profiling of Synthetic Acylphloroglucinol Scaffolds.Angewandte Chemie (International ed. in English) · 2021Article
- Programmable meroterpene synthesis.Nature communications · 2020Article
- Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.Angewandte Chemie (International ed. in English) · 2019Article
- Regiodivergent Photocyclization of Dearomatized Acylphloroglucinols: Asymmetric Syntheses of (-)-Nemorosone and (-)-6-Journal of the American Chemical Society · 2019Article
- Local Desymmetrization through Diastereotopic Group Selection: An Enabling Strategy for Natural Product Synthesis.European journal of organic chemistry · 2017Article
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3 authors.
Funding
Abstract
The first syntheses of 13,14-didehydroxyisogarcinol (6) and garcimultiflorone A (5) stereoisomers are reported in six steps from a commercially available phloroglucinol. Lewis acid-controlled, diastereoselective cationic oxycyclizations enabled asymmetric syntheses of (-)-6-epi-6 and (+)-30-epi-6. A similar strategy enabled production of the meso-dervied isomers (±)-6,30-epi-6 and (±)-6,30-epi-5. Finally, a convenient strategy for gram scale synthesis was developed utilizing diastereomer separation at a later stage in the synthesis that minimized the number of necessary synthetic operations to access all possible stereoisomers.
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