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Prins Cyclizations: Labeling Studies and Application to Natural Product Synthesis

2002; American Chemical Society; Volume: 4; Issue: 20 Linguagem: Inglês

10.1021/ol020127o

1523-7060

Stuart R. Crosby, John Harding, Clare D. King, Gregory D. Parker, Christine L. Willis,

Traditional and Medicinal Uses of Annonaceae

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.