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Synlett 1993; 1993(7): 494-496
DOI: 10.1055/s-1993-22503
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Stereochemical Prediction in Macrocyclic Enone Switching Based on Molecular Mechanics Calculation

Takashi Takahashi* , Hajime Yokoyama, Haruo Yamada, Takeharu Haino, Yoshimasa Fukazawa
  • *Department of Chemical Engineering, Tokyo Institute of Technology, Okayama, Meguro, Tokyo 152, Japan
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Publication Date:
19 March 2002 (online)

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Synthesis of the exocyclic 14-membered enone 4 by dianion cyclization and enone switching reaction of the exo-enone 4 with lithium dimethyl cuprate to provide the Z-enone 3 are described. The stereochemical course of the macrocyclic enone switching is discussed based on MM2 calculations.