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
- 28 February 2018
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 83 (7) , 4167-4172
Abstract
(R)-Paraconyl alcohol is found to be a key intermediate for the syntheses of many γ-butyrolactone autoregulators. 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 a first organocatalytic approach for the short asymmetric synthesis of (R)-paraconyl alco-hol in four steps and single column purification. Asymmetric syntheses of IM-2, SCB2 and A-factor γ-butyrolactone autoregula-tors were achieved from (R)-paraconyl alcohol in three steps.Keywords
Funding Information
- Indian Institute of Technology Gandhinagar
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