Publikation

T. Krüger, A. Bramborg, A. Kelling, E. Sperlich, T. Linker
Birch Reduction of Arenes as an Easy Entry to γ-Spirolactones
Eur. J. Org. Chem. 2021, 6383-6391
DOI: 10.1002/ejoc.202101018
A convenient method for the synthesis of γ-spirolactones in only 2–3 steps is described. Birch reduction of inexpensive and commercially available aromatic carboxylic acids in the presence of ethyleneoxide affords hydroxyacids, which undergo direct lactonization during work-up. Suitable precursors are methyl-substituted benzoic acids, naphthoic, and dicarboxylic acids. Subsequent hydrogenation proceeds smoothly with Pd/C as catalyst and saturated γ-spirolactones are isolated in excellent yields and stereoselectivities. Thus, up to 3 new stereogenic centers can be constructed as sole diastereomers from achiral benzoic acids. Furthermore, it is possible to control the degree of saturation with \r\nRaney nickel or Wilkinson\'s catalyst to obtain products with 1 double bond. Overall, more than 30 new γ-spirolactones have been synthesized in analytically pure form.
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