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Prins cyclizations: labeling studies and application to natural product synthesis
Stuart R Crosby1, John R Harding, Clare D King
1School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K.
Organic Letters
|September 27, 2002
Abstract:
The first syntheses of two natural products, catechols 1 and 2, isolated from Plectranthus sylvestris (labiatae), are reported. Oxygen-18 labeling studies support the proposed intermediacy of a stabilized benzylic cation in the acid-promoted cyclization of an aldehyde and benzylic homoallylic alcohol possessing an electron-rich aromatic ring. In contrast, with an electron-deficient aromatic ring the pathway via a benzylic cation is only minor. [reaction: see text]