Organocatalytic Approach for Short Asymmetric Synthesis of (R)-Paraconyl Alcohol: Application to the Total Syntheses of IM-2, SCB2, and A-Factor γ-Butyrolactone Autoregulators
2018
Sarkale, Abhijeet M. | Kumar, Amit | Appayee, Chandrakumar
(R)-Paraconyl alcohol is found to be a key intermediate for the syntheses of many γ-butyrolactone autoregulators. The chiral auxiliary approach and enzymatic resolution are the two common strategies employed so far in the literature for the asymmetric synthesis of (R)-paraconyl alcohol. Herein, we report the first organocatalytic approach for the short asymmetric synthesis of (R)-paraconyl alcohol in four steps and by a single column purification. Asymmetric syntheses of IM-2, SCB2, and A-factor γ-butyrolactone autoregulators were achieved from (R)-paraconyl alcohol in three steps.
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