190077-90-8Relevant academic research and scientific papers
Prins cyclizations: labeling studies and application to natural product synthesis.
Crosby, Stuart R,Harding, John R,King, Clare D,Parker, Gregory D,Willis, Christine L
, p. 3407 - 3410 (2007/10/03)
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]
