An improved protocol for the Prins desymmetrisation of cyclohexa-1,4-dienes |
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| Authors: | Michael Butters Joseph Hill-Cousins Alexander W.J. Westwood |
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| Affiliation: | a School of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK
b AstraZeneca Process R&D Avlon/Charnwood, Avlon Works, Severn Road, Hallen, Bristol BS10 7ZE, UK |
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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. |
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