Stereoselective Synthesis of <i>trans</i>‐Decalins via Intramolecular Ene Reactions; Synthesis of the Enantiomerically Pure Cadinane‐Sesquiterpene Veticadinol — Lutz F. Tietze (1988) | RDL Network
Stereoselective Synthesis of <i>trans</i>‐Decalins via Intramolecular Ene Reactions; Synthesis of the Enantiomerically Pure Cadinane‐Sesquiterpene Veticadinol
Angewandte Chemie International Edition 27(5): 703-705
Article 1988 English
Authors
LT
Lutz F. Tietze
UB
Uwe Beifuß
JA
Jack P. Antel
Abstract
1 min read
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 FeCl3 on Al2O3, which is readily available and gives very good selectivities as well as high yields.
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