Transannular Cyclization of Epoxycaryophyllenes Catalyzed by Ti III : An Efficient Synthesis of Tricyclo[6.3.0.0 2,5 ]undecanes | Zendy

Barrero Alejandro F. | Zendy; Herrador M. Mar | Zendy; Quílez del Moral José F. | Zendy; Arteaga Pilar | Zendy; Sánchez Elena M. | Zendy; Arteaga Jesús F. | Zendy; Piedra Maria | Zendy

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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

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)

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