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Access to benzene-modified 2nd generation strigolactams and GR24 by merging C–H olefination with decarboxylative Giese cyclization†
Yuhua Ge,Xingyue Chen,Yi Dong,Hua-Nan Wang,Gang Chen
Organic & Biomolecular Chemistry Pub Date : 07/27/2021 00:00:00 , DOI:10.1039/D1OB01234G
Abstract

Herein, we reported an efficient and general synthetic route to assemble benzene-modified 2nd 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. 2nd generation strigolactam 15f derived from para-OMe phenylalanine showed superior bioactivity to the original unsubstituted 15b.

Graphical abstract: Access to benzene-modified 2nd generation strigolactams and GR24 by merging C–H olefination with decarboxylative Giese cyclization
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