Solvolysis of a Tetrahydropyranyl Mesylate: Mechanistic Implications for the Prins Cyclization, 2-Oxonia-Cope Rearrangement, and Grob Fragmentation
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چکیده
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2-Arylcyclopropylmethanol as a substitute for homoallyl aryl alcohol in the construction of cis-2,6-disubstituted tetrahydropyran: synthesis of (±)-centrolobine.
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...
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2006
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol0606738