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RESEARCH PRODUCT
Total Synthesis of Phenanthroindolizidine Alkaloids by Combining Iodoaminocyclization with Free Radical Cyclization
Till OpatzGong-qing LiuMarcel Reimannsubject
IndolesMagnetic Resonance SpectroscopyPyrrolidinesFree RadicalsChemistry OrganicStereoisomerism010402 general chemistry01 natural sciencesRadical cyclizationStructure-Activity RelationshipAlkaloidsOrganic chemistry010405 organic chemistryChemistryOrganic ChemistryIndolizinesTemperatureTotal synthesisStereoisomerismNuclear magnetic resonance spectroscopyPhenanthrenesIsoquinolines0104 chemical sciencesCyclizationYield (chemistry)Phenanthrolinesdescription
A concise and modular synthesis of phenanthroindolizidine alkaloids was achieved by combining iodoaminocylization with a free radical cyclization approach. The route described allowed the preparation of (±)-tylophorine, (±)-antofine, and (±)-deoxypergularinine in six steps. When commercially available l-prolinol was used as a chiral building block, (S)-(+)-tylophorine was also synthesized in 49% yield and >99% ee over five linear steps.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-06-18 | The Journal of Organic Chemistry |