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Synthesis 1987; 1987(8): 705-708
DOI: 10.1055/s-1987-28051
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A New Route to a Chiral Synthon for the Total Synthesis of Estrone

Andrzej Robert Daniewski* , Jarosław Kiegiel
  • *Institute of Organic Chemistry, Polish Academy of Sciences, PL-01-224 Warsaw, Poland
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Publikationsdatum:
12. September 2002 (online)

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(2S,3S)-2-(2-Bromoethyl)-3-ethenyl-2-methylcyclopentanone 2,2-dimethyl-1, 3-propanediyl acetal (Synthon C) is a chiral synthon for the total synthesis of estrone. Synthon C is prepared from 3a-hydroxy-7a-methyloctahydroindeno-1, 5-dione by a multistep sequence, the key steps of which consist of the regioselective Baeyer-Villiger oxidation of the starting dione and the stereospecific catalytic hydrogenation of an intermediate unsaturated bicyclic lactone.