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 |
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| container_title | Organic letters |
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| creator | Crosby, Stuart R Harding, John R King, Clare D Parker, Gregory D Willis, Christine L |
| description | 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. |
| doi_str_mv | 10.1021/ol020127o |
| format | Article |
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| ispartof | Organic letters, 2002-10, Vol.4 (20), p.3407-3410 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| 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 |
| title | Prins Cyclizations: Labeling Studies and Application to Natural Product Synthesis |
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