The stereoselective synthesis of cis-/trans-fused hexahydropyrano[4,3-b]chromenes via Prins cyclization trapping by a tethered nucleophile |
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| Authors: | B V Subba Reddy Sayed Jalal Prashant Borkar J S Yadav P P Reddy A C Kunwar B Sridhar |
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| Institution: | Natural Product Chemistry, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad 500607, India. basireddy@iict.res.in |
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| Abstract: | A novel intramolecular Prins cyclization of (Z)-2-(5-hydroxypent-2-enyl)phenol with various aldehydes has been achieved using 10 mol% In(OTf)(3) and 30 mol% TsOH to produce the cis-fused hexahydropyrano4,3-b]chromene derivatives in good yields, while the coupling of (E)-2-(5-hydroxypent-2-enyl)phenol with aldehydes under similar conditions affords the corresponding trans-fused hexahydropyrano4,3-b]chromene derivatives. |
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