Issue 32, 2012

The stereoselective synthesis of cis-/trans-fused hexahydropyrano[4,3-b]chromenes via Prins cyclization trapping by a tethered nucleophile

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 hexahydropyrano[4,3-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 hexahydropyrano[4,3-b]chromene derivatives.

Graphical abstract: The stereoselective synthesis of cis-/trans-fused hexahydropyrano[4,3-b]chromenes via Prins cyclization trapping by a tethered nucleophile

Supplementary files

Article information

Article type
Paper
Submitted
23 Apr 2012
Accepted
01 Jun 2012
First published
01 Jun 2012

Org. Biomol. Chem., 2012,10, 6562-6568

The stereoselective synthesis of cis-/trans-fused hexahydropyrano[4,3-b]chromenes via Prins cyclization trapping by a tethered nucleophile

B. V. Subba Reddy, S. Jalal, P. Borkar, J. S. Yadav, P. P. Reddy, A. C. Kunwar and B. Sridhar, Org. Biomol. Chem., 2012, 10, 6562 DOI: 10.1039/C2OB25771H

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