Abstract
AbstractA new cyclopentene annulation method based on a conjugate addition reaction with 4‐methoxybut‐3‐enenitrile was developed. Treatment of a cyclic enone with the potassium carbanion of the nitrile followed by acetic anhydride afforded an enol acetate, which underwent an HCl‐mediated intramolecular cyclization reaction to yield a bicyclo[n.3.0]alkenone derivative in good yield. A lipase‐mediated optical resolution of the annulation product provided a new chiral building block for steroids and other natural compounds.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
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