2019
DOI: 10.1002/chem.201904223
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Formal Synthesis of Indolizidine and Quinolizidine Alkaloids from Vinyl Cyclic Carbonates

Abstract: Cyclic carbonates have long been considered relatively inert molecules acting as protecting groups in complex multistep synthetic routes. This study shows that a concise, yet modular synthesis of indolizidine and quinolizidine alkaloids can be developed from vinyl‐substituted cyclic carbonate (VCC) intermediates. Through a highly stereoselective palladium‐catalyzed allylic alkylation reaction, these alkaloid motifs can be assembled in four synthetic and only two column purification steps. The combined results … Show more

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Cited by 13 publications
(11 citation statements)
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“…Contemporary research in the area of carbon dioxide (CO 2 ) valorization catalysis has offered a plethora of new transformations toward products with value in fine chemical synthesis, pharmaceutical development, , and polymer science. Without a doubt, nonreductive catalytic conversions of CO 2 are among the most widely studied transformations. These reactions contemplate on the consensus that the thermodynamic challenge in the conversion of this carbon feedstock is best met by using higher-energy reactants such as strained molecules.…”
Section: Introductionmentioning
confidence: 99%
“…Contemporary research in the area of carbon dioxide (CO 2 ) valorization catalysis has offered a plethora of new transformations toward products with value in fine chemical synthesis, pharmaceutical development, , and polymer science. Without a doubt, nonreductive catalytic conversions of CO 2 are among the most widely studied transformations. These reactions contemplate on the consensus that the thermodynamic challenge in the conversion of this carbon feedstock is best met by using higher-energy reactants such as strained molecules.…”
Section: Introductionmentioning
confidence: 99%
“…Synthetic routes for the models in Scheme 2 and authentic compounds for the HPLC analysis are shown in Schemes S1–S4 in the ESI †. All the compounds were synthesized according to the route reported in the literature: 37,53,64,65 ref. 37 for VGL , ref.…”
Section: Methodsmentioning
confidence: 99%
“…Strategically, every one-pot method involving SO 2 F 2 has relied upon alkyl fluorosulfate intermediate 2 as the key reactive intermediate (Scheme ). This has limited the reactions that can be accessed to substitutions and substitutions combined with subsequent oxidations and/or eliminations . Even for the successful one-pot methods, the high reactivity of fluorosulfate 2 places significant limitations on the scope with respect to both the alcohol and the nucleophile.…”
Section: Introductionmentioning
confidence: 99%