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Transannular Cyclization of Epoxycaryophyllenes Catalyzed by Ti III : An Efficient Synthesis of Tricyclo[6.3.0.0 2,5 ]undecanes
Author(s) -
Barrero Alejandro F.,
Herrador M. Mar,
Quílez del Moral José F.,
Arteaga Pilar,
Sánchez Elena M.,
Arteaga Jesús F.,
Piedra Maria
Publication year - 2006
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.200600159
Subject(s) - chemistry , undecane , catalysis , radical cyclization , stereochemistry , medicinal chemistry , organic chemistry
Abstract The transannular cyclization of epoxycaryophyllenes 2 – 7 catalyzed by Ti III has been investigated. This cyclization led to alcohols 8 – 15 , all of them possessing a tricyclo[6.3.0.0 2,5 ]undecane skeleton. All of these compounds present pleasant aromatic properties. The cyclization takes place with high yields (> 80 %) and via the αα or ββ conformation of the intermediate radical I . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)