The first asymmetry synthesis of glutinone and its three diastereoisomers were carried out in 8 steps and the stereochemistry of this natural product was given out.
The four isomers of 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid 2 were synthesized via the selective direct Sharpless asymmetry dihydroxylation of geraniol as the key step in 35.0%-48.0% overall yields with91.9%-97.7% ...The four isomers of 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid 2 were synthesized via the selective direct Sharpless asymmetry dihydroxylation of geraniol as the key step in 35.0%-48.0% overall yields with91.9%-97.7% ee values for esters 4 and 31,3%-36.4% overall yields with 90.3-97.5% ee values for acids 2 using cis-and trans-geraniol as raw materials. Their structures were characterized by;H,;C NMR and HR-ESI-MS data. The in vivo bioassay results showed that the chiral acid（Z, S）-2 was a good lead compound with 80%-100% inhibitory rates against P. cubensis, E. graminis, P. sorghi and C. gloeosporioides at the concentration of 400 μg/mL.展开更多
基金We are grateful for financial support from the National Natural Science Foundation of China (Grant No. 29732060)
文摘The first asymmetry synthesis of glutinone and its three diastereoisomers were carried out in 8 steps and the stereochemistry of this natural product was given out.
基金the National Natural Science Foundation of China(Nos.21772229,21172254)for the financial support
文摘The four isomers of 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid 2 were synthesized via the selective direct Sharpless asymmetry dihydroxylation of geraniol as the key step in 35.0%-48.0% overall yields with91.9%-97.7% ee values for esters 4 and 31,3%-36.4% overall yields with 90.3-97.5% ee values for acids 2 using cis-and trans-geraniol as raw materials. Their structures were characterized by;H,;C NMR and HR-ESI-MS data. The in vivo bioassay results showed that the chiral acid（Z, S）-2 was a good lead compound with 80%-100% inhibitory rates against P. cubensis, E. graminis, P. sorghi and C. gloeosporioides at the concentration of 400 μg/mL.
