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Stereoselective Synthesis of trans ‐Decalins via Intramolecular Ene Reactions; Synthesis of the Enantiomerically Pure Cadinane‐Sesquiterpene Veticadinol
Author(s) -
Tietze Lutz F.,
Beifuss Uwe,
Antel Jochen,
Sheldrick George M.
Publication year - 1988
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198807031
Subject(s) - intramolecular force , ene reaction , knoevenagel condensation , chemistry , citronellal , stereoselectivity , alkylation , malonate , organic chemistry , carbanion , diethyl malonate , aldol condensation , catalysis , medicinal chemistry
Knoevenagel condensation, intramolecular ene reaction, demethoxycarbonylation, Prins reaction, intramolecular alkylation and Grignard reaction ‐‐starting from ( R )‐citronellal 2 and dimethyl malonate 1 , these reaction steps lead stereoselectively to veticadinol 3 . A new catalyst was used for the ene reaction, namely FeCl 3 on Al 2 O 3 , which is readily available and gives very good selectivities as well as high yields.