Total Synthesis of (+)-Guadinomic Acid via Hydroxyl-Directed Guanidylation

Total Synthesis of (+)-Guadinomic Acid via Hydroxyl-Directed Guanidylation

Protecting-group-free total synthesis of (+)-guadinomic acid is reported using δ-valerolactone as a readily available starting material. The protocol utilizes the recent hydroxyl-directed guanidylation of unactivated alkenes as an approach for direct stereoselective incorporation of the guanidine un...

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Veröffentlicht in:Journal of organic chemistry 2018-08, Vol.83 (16), p.9492-9496
Hauptverfasser: Reid, Bradley T, Mailyan, Artur K, Zakarian, Armen
Format: Artikel
Sprache:eng
Schlagworte:
Caproates - chemical synthesis
Caproates - chemistry
Catalysis
Chemistry Techniques, Synthetic
Guanidine - chemistry
Hydroxyl Radical - chemistry
Imidazolidines - chemical synthesis
Imidazolidines - chemistry
Stereoisomerism
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Zusammenfassung:Protecting-group-free total synthesis of (+)-guadinomic acid is reported using δ-valerolactone as a readily available starting material. The protocol utilizes the recent hydroxyl-directed guanidylation of unactivated alkenes as an approach for direct stereoselective incorporation of the guanidine unit furnishing the natural product in 7 steps.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01214