Synthesis and Rearrangement of Quinone-Embedded Epoxycyclopentenones: A New Avenue to Pyranonaphthoquinones and Indenopyranones

The epoxyquinones (e.g., 24), readily assembled in one step from the quinols (e.g., 27) by a simplified version of the Dowd oxidation, are shown to undergo rearrangement to pyranonaphthoquinones (e.g., 28) and their ring contracted homologues (e.g., 29) on flash vacuum pyrolysis at 450 °C and 0.01 T...

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Veröffentlicht in:Journal of organic chemistry 2009-02, Vol.74 (4), p.1598-1604
Hauptverfasser: De, Saroj R, Ghorai, Sujit K, Mal, Dipakranjan
Format: Artikel
Sprache:eng
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Zusammenfassung:The epoxyquinones (e.g., 24), readily assembled in one step from the quinols (e.g., 27) by a simplified version of the Dowd oxidation, are shown to undergo rearrangement to pyranonaphthoquinones (e.g., 28) and their ring contracted homologues (e.g., 29) on flash vacuum pyrolysis at 450 °C and 0.01 Torr. The rearrangement has been demonstrated to be useful for a regiospecific synthesis of lambertellin (3). Similarly, the masked aziridinocyclopentanone 9 rearranges to 2-pyridone (37).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo801961w