Intramolecular cyclopentene annulation. 3. Synthesis and carbon-13 nuclear magnetic resonance spectroscopy of bicyclic cyclopentene lactones as potential …

T Hudlicky, DB Reddy, SV Govindan…

Index: Hudlicky, Tomas; Reddy, D. Bhaskar; Govindan, S. V.; Kulp, Thomas; Still, Bobbi; Sheth, Jagdish P. Journal of Organic Chemistry, 1983 , vol. 48, # 20 p. 3422 - 3428

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Citation Number: 43

Abstract

The internal cyclopropanation of several diversely substituted dienic diazo esters is described. Thermolysis of the resulting vinylcyclopropanes yielded cyclopentene-annulated lactones in good yields. Depending on the choice of the dienyl unit, either guaiane or pseudoguaiane substitution patterns of the cyclopentene portion were obtained. Stereochemical assignments based on 13C NMR data are provided for all of these ...