An improved protocol for the Prins desymmetrization of cyclohexa-1,4-dienes

Butters, Michael, Elliott, Mark Christopher ORCID: https://orcid.org/0000-0003-0132-0818, Hill-Cousins, Joseph Thomas, Paine, James Stephen and Westwood, Alexander William J. 2008. An improved protocol for the Prins desymmetrization of cyclohexa-1,4-dienes. Tetrahedron Letters 49 (28) , pp. 4446-4448. 10.1016/j.tetlet.2008.05.022

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Abstract

Improved conditions are reported for the Prins-pinacol rearrangement of cyclohexa-1,4-diene-derived acetals. The use of triflic acid gives particularly clean reaction, resulting in a mixture of regioisomers in an approximately 10:1 ratio. A tethered version of this reaction is also reported, giving a tricyclic compound with the same stereochemistry as the core of the cladiellin diterpenes.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Elsevier
ISSN:	0040-4039
Last Modified:	02 Jan 2025 15:43
URI:	https://orca.cardiff.ac.uk/id/eprint/5881

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