2-Arylcyclopropylmethanol as a substitute for homoallyl aryl alcohol in the construction of cis-2,6-disubstituted tetrahydropyran: synthesis of (±)-centrolobine?
Chemical Communications Pub Date: 2014-10-20 DOI: 10.1039/C4CC07796B
Abstract
The application of 2-arylcyclopropylmethanols as substitutes to homoallyl aryl alcohols and their reactions with aliphatic aldehydes in the presence of SnCl4 in CH2Cl2 leads to an efficient Prins cyclization to generate cis-2,6-disubstituted tetrahydropyrans in high yields. The reaction is free from 2-oxonia-Cope rearrangement. This protocol was used to synthesize (±)-centrolobine in an overall 84% yield over three steps. The protocol holds promise for scaffold generation for medicinal chemistry exploitation.
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Journal Name：Chemical Communications
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CAS no.: 89640-58-4
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