Synthesis of (-)-pinolidoxin: divergent synthetic strategy exploiting a common silacyclic precursor.
[reaction: see text] We describe a highly convergent and efficient synthesis of (-)-pinolidoxin, a potent modulator of plant pathogenesis, providing unambiguous determination of the relative and absolute stereostructure of this highly oxygenated fungal metabolite. Our unique strategy highlights the applications of novel silacyclic precursors for stereocontrolled polyol synthesis and features the finding of the reversible ring-closing metathesis.
Liu
Dong
D
The University of Chicago, Department of Chemistry, 5735 South Ellis Ave., Chicago, Illinois 60637, USA.
Kozmin
Sergey A
SA
D000475:Alkenes / Q000138:chemical synthesis*; D001203:Ascomycota / Q000737:chemistry; D005658:Fungi / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis*; D015394:Molecular Structure; D010650:Phenylalanine Ammonia-Lyase / Q000037:antagonists & inhibitors; D017655:Silicon Compounds / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D007659:Ketones; D017655:Silicon Compounds; C410769:pinolidoxin; D010650:Phenylalanine Ammonia-Lyase