Access to benzene-modified 2 generation strigolactams and GR24 by merging C-H olefination with decarboxylative Giese cyclization

Herein, we reported an efficient and general synthetic route to assemble benzene-modified 2 nd generation strigolactams and GR24. The key features of this synthesis include a palladium-catalyzed ortho -selective olefination of the commercially available substituted N -Boc phenylalanine and a decarbo...

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Veröffentlicht in:Organic & biomolecular chemistry 2021-09, Vol.19 (33), p.7141-7146
Hauptverfasser: Ge, Yuhua, Chen, Xingyue, Dong, Yi, Wang, Hua-Nan, Li, Yangyan, Chen, Gang
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Sprache:eng
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Zusammenfassung:Herein, we reported an efficient and general synthetic route to assemble benzene-modified 2 nd generation strigolactams and GR24. The key features of this synthesis include a palladium-catalyzed ortho -selective olefination of the commercially available substituted N -Boc phenylalanine and a decarboxylative Giese radical cyclization. The bioactivities of these compounds to stimulate the seed germination of Orobanche aegyptiaca parasitic weed were also analysed. 2 nd generation strigolactam 15f derived from para -OMe phenylalanine showed superior bioactivity to the original unsubstituted 15b . Herein, we reported an efficient and general synthetic route to assemble benzene-modified 2 nd generation strigolactams and GR24. The key features of this synthesis include a palladium-catalyzed ortho -selective olefination and a decarboxylative Giese radical cyclization.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01234g