A facile three-component one-pot synthesis of structurally constrained tetrahydrofurans that are t-RNA synthetase inhibitor analogues.
A one-pot procedure for the efficient synthesis of tRNA inhibitor analogues was developed. Thus, three-component 1,3-dipolar cycloaddition reactions of carbonyl ylides derived from diazoindan-1,3-dione and aldehydes with other dipolarophiles in 1,1,2,2-tetrachloroethane in 80 degrees C gave ring-fused tetrahydrofurans having three stereocenters in good yield.
Lu
Chong-Dao
CD
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
Chen
Zhi-Yong
ZY
Liu
Hui
H
Hu
Wen-Hao
WH
Mi
Ai-Qiao
AQ
Doyle
Michael P
MP
D000604:Amino Acyl-tRNA Synthetases / Q000037:antagonists & inhibitors*; D018360:Crystallography, X-Ray; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013696:Temperature
D004791:Enzyme Inhibitors; D005663:Furans; D000604:Amino Acyl-tRNA Synthetases