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. 2002 Oct 3;4(20):3407-10.
doi: 10.1021/ol020127o.

Prins cyclizations: labeling studies and application to natural product synthesis

Stuart R Crosby  1 , John R Harding, Clare D King, Gregory D Parker, Christine L Willis
Affiliations

Prins cyclizations: labeling studies and application to natural product synthesis

Stuart R Crosby et al. Org Lett. .

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]

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