The keto-acid 5 undergoes stereospecific Peterson reaction to afford the (Z)-α-unsaturated ester-acid 6, and the derived phenyl selenoester cyclises also stereospecifically to the cis-hydrindanone 8via a 5-exo acyl radical process: the ketone 8 is transformed through enone 11 into the diene-acids 2 and 3, models for study of C-18 radical reactions in steroid C/D systems.
S. P. Green and D. A. Whiting, J. Chem. Soc., Chem. Commun., 1992, 1753 DOI: 10.1039/C39920001753
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