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Updated: Jun 28, 2025

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A synthesis of (±)-thia-calanolide A, its resolution and in vitro biological evaluation
Anil U Chopade1, Manojkumar U Chopade2, Bhanu M Chanda1
1Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India.
Abstract:
A synthesis of (±)-thia-calanolide A 3 has been successfully accomplished starting from 3,5-dimethoxythiophenol 4, in six steps in an overall yield of 4.5%. The key reaction involved Friedel-Crafts tigloylation of 5,7-dihydroxy-4-n-propyl thiocoumarin 6 employing an appropriate solvent of CS2-PhNO2 in a ratio of 7:3. In its biological evaluation for anti-HIV activity, (±)-thia-calanolide A 3 demonstrated comparatively less activity with calanolide A and its synthetic analogue aza-calanolide. Further, (±)-3 has been resolved by chiral HPLC to (+) and (-)-3.
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