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Titanocene(III)‐Catalyzed 6‐ exo Versus 7‐ endo Cyclizations of Epoxypolyprenes: Efficient Control and Synthesis of Versatile Terpenic Building Blocks
Author(s) -
Justicia José,
Jiménez Tania,
Miguel Delia,
ContrerasMontoya Rafael,
Chahboun Rachid,
ÁlvarezManzaneda Enrique,
ColladoSanz Daniel,
Cárdenas Diego J.,
Cuerva Juan M.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201302575
Subject(s) - selectivity , terpene , catalysis , chemistry , derivative (finance) , combinatorial chemistry , tricyclic , stereochemistry , organic chemistry , economics , financial economics
In this article, a complete study on the selectivity of titanocene(III) cyclization of epoxypolyprenes is presented. The requirements for the formation of six‐ or seven‐membered rings during these cyclizations are determined, taking into account the different substitution pattern in the epoxypolyprene precursor. Thus, a complete selectivity to 6‐ exo or 7‐ endo cyclization process has been achieved, yielding mono‐, bi‐, and even tricyclic compounds, constituting a new and efficient access to this type of derivative. Additionally, this procedure opens the possibility to prepare excellent building blocks for the synthesis of polycyclic compounds with a trisubstituted oxygenated function, which is present in several natural terpenes.