Novel C3V-symmetric tripodal scaffold, triethyl cis,cis,cis-2,5,8- tribenzyltrindane-2,5,8-tricarboxylate, for the construction of artificial receptors.
[reaction: see text] A novel C3V-symmetric scaffold, trindane 7, has been efficiently synthesized from 1,3,5-tris(bromomethyl)-2,4,6-tris(chloromethyl)benzene (1) in six steps with 47% overall yield. The control of all-syn stereochemistry in the tribenzylation step has been achieved by blocking one side of the trindane ring as metal carbonyl complexes. The potential utility of trindane 7 as a receptor skeleton has been examined with a urea derivative 12 toward several anionic guests.
Choi
Heung-Jin
HJ
Department of Industrial Chemistry and Department of Chemical Engineering, Kyungpook National University, Daegu 702-701, Korea. choihj@knu.ac.kr
Park
Yeon Sil
YS
Yun
Seok Hun
SH
Kim
Hong-Seok
HS
Cho
Chan Sik
CS
Ko
Kwangnak
K
Ahn
Kyo Han
KH
D000838:Anions / Q000032:analysis* / Q000737:chemistry / Q000378:metabolism; D001665:Binding Sites; D015374:Biosensing Techniques / Q000379:methods*; D008958:Models, Molecular; D008968:Molecular Conformation; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics; D011955:Receptors, Drug / Q000737:chemistry*; D012997:Solvents; D017186:Titrimetry
D000838:Anions; D011083:Polycyclic Compounds; D011955:Receptors, Drug; D012997:Solvents; C467075:triethyl-2,5,8- tribenzyltrindane-2,5,8-tricarboxylate