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Ein neuer Zugang zum tetracyclischen Grundgerüst des Cyclohepta ( def )fluorens
Author(s) -
Neidlein Richard,
Kramer Walter
Publication year - 1981
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.19810640329
Subject(s) - chemistry , fluorene , ketone , yield (engineering) , butyllithium , hydrocarbon , medicinal chemistry , stereochemistry , organic chemistry , materials science , metallurgy , polymer
A New Synthetic Way to the Tetracyclic Skeleton of Cyclohepta ( def )fluorene The synthesis of 2‐Methyl‐4, 5, 6, 8, 9, 10‐hexahydrocyclohepta ( def )fluorene 2 is described starting with the reduction of the ketone 3 by a (1:1)‐mixture of LiAlH 4 /AlCl 3 to the hydrocarbon 4 . After metallation with butyllithium 4 was allowed to react with bromoacetic acid to yield 5 . The cyclization of this compound was performed with p ‐toluenesulfonic acid to give the tetracyclic ketone 6 which was converted to the tetracyclic hydrocarbon 2 by reduction with LiAlH 4 /AlCl 3 .