Prins Cyclizations:  Labeling Studies and Application to Natural Product Synthesis

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 alcoho...

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Bibliographic Details
Published in:Organic letters 2002-10, Vol.4 (20), p.3407-3410
Main Authors: Crosby, Stuart R, Harding, John R, King, Clare D, Parker, Gregory D, Willis, Christine L
Format: Article
Language:English
Subjects:
Anti-Inflammatory Agents - chemical synthesis
Antioxidants - chemical synthesis
Biological Factors - chemical synthesis
Catechols - chemical synthesis
Cyclization
Lamiaceae - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol020127o