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Studies Towards Anti-Bredt Ring Systems Of Natural Products, Ulf Peters
Studies Towards Anti-Bredt Ring Systems Of Natural Products, Ulf Peters
Masters Theses
Different ways for the synthesis of anti-Bredt ring systems of natural products have been explored.
An intended Favorskii rearrangement-divinylcyclopropane rearrangement to lead to the bicyclo[4.3.1] decadiene ring system was not accomplished. An envisioned tandem cyclopropanation-divinycyclopropane rearrangement of 2,3-divinyhex-2-enol did not furnish the desired bicyclo[4.4.1]undecadiene system, either, because cyclopropane occurred on the exocyclic double bond.
In the course of cyclopropanation studies on various cyclohexenols, an α-silyl-α-diazoethyl acetate was employed as tether. It could be removed by protodesilylation or oxidative cleavage to give a 1-(carboxylic ester)-cyclopropane or a 1-(carboxylic easter)-1-hydroxy cyclopropane derivative, respectively. Cyclopropanation general occurred on the less substituted more …