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Electrophilic Cyclization and Ring‐Closing Metathesis as Key Steps in the Synthesis of a 12‐Membered Cyclic Enediyne
Author(s) -
Danilkitalia,
Nieger Martin,
Selivanov Stanislav,
Bräse Stefan,
Balova Irina
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200881
Subject(s) - enediyne , chemistry , ring closing metathesis , electrophile , metathesis , stereochemistry , ring (chemistry) , enantiomer , combinatorial chemistry , organic chemistry , polymerization , catalysis , polymer
Abstract For the first time, electrophilic cyclization and ring‐closing metathesis were used as key steps in the synthesis of a macrocyclic enediyne system, which allowed a 12‐membered dienediyne containing a thiophene‐fused ring to be obtained. The macrocycle synthesized represents a class of compounds that possess planar chirality and exists in the solid state as two enantiomers, whereas in solution the rate of interconversion is rapid as a result of unhindered switching of the double bond through the macrocycle.