76 research outputs found
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
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.R01 GM073855 - NIGMS NIH HHS; R24 GM111625 - NIGMS NIH HHS; R35 GM118173 - NIGMS NIH HH
ChemInform Abstract: The Asymmetric Hetero-Diels-Alder Reaction in the Syntheses of Biologically Relevant Compounds
ChemInform Abstract: An Enantioselective Inverse-Electron-Demand Imino Diels-Alder Reaction.
Development of Cascade Reactions to Ring-Fused Quinolizines for the Synthesis of a Natural Product-Inspired Compound Collection
Die asymmetrische Hetero-Diels-Alder-Reaktion in Synthesen biologisch relevanter Verbindungen
The Asymmetric Hetero-Diels-Alder Reaction in the Syntheses of Biologically Relevant Compounds
Wolf-Preis in Chemie: C.-H. Wong / Gay-Lussac-Humboldt-Preis: A. Fürstner / New Investigator Award in organischer Chemie: D. Nicewicz / Ehrendoktorwürde: H. Waldmann
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