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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Veröffentlicht in:	Organic letters 2002-10, Vol.4 (20), p.3407-3410
Hauptverfasser:	Crosby, Stuart R, Harding, John R, King, Clare D, Parker, Gregory D, Willis, Christine L
Format:	Artikel
Sprache:	eng
Schlagworte:	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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Beschreibung
Zusammenfassung:	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