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Cyclotrimerization of ‘Oxabenzonorbornadiene’: Synthesis of syn ‐ and anti ‐5,6,11,12,17,18‐Hexahydro‐5,18:6,11:12,17‐triepoxytrinaphthylene
Author(s) -
De Lucchi Ottorino,
Daştan Arif,
Altundaş Aliye,
Fabris Fabrizio,
Balci Metin
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490213
Subject(s) - chemistry , thiophene , copper , carboxylate , catalysis , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry
Abstract An efficient synthetic route to the concave‐shaped, potentially ionophoric syn ‐ and anti ‐isomers of 5,6,11,12,17,18‐hexahydro‐5,18:6,11:12,17‐triepoxytrinaphthylene ( 4 ) was elaborated. Starting from ‘oxabenzonorbornadiene’ ( 5 ), the stannylated precursor 9 was prepared in three steps, followed by cyclotrimerization catalyzed by copper(I) thiophene‐2‐carboxylate (CuTC) , which afforded 4 in a syn / anti ratio of 5 : 4.