Cyclotrimerization of ‘Oxabenzonorbornadiene’: Synthesis of  syn ‐ and  anti ‐5,6,11,12,17,18‐Hexahydro‐5,18:6,11:12,17‐triepoxytrinaphthylene | Zendy

De Lucchi Ottorino | Zendy; Daştan Arif | Zendy; Altundaş Aliye | Zendy; Fabris Fabrizio | Zendy; Balci Metin | Zendy

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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

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.

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