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

[摘要]：Epoxyquinones (e.g., I), readily assembled in one step from the quinols (e.g., II) by a simplified version of the Dowd oxidn., are shown to undergo rearrangement to pyranonaphthoquinones (e.g., III) and their ring contracted homologs (e.g., IV) on flash vacuum pyrolysis at 450癈 and 0.01 Torr. The rearrangement has been demonstrated to be useful for a regiospecific synthesis of lambertellin. Similarly, the masked aziridinocyclopentanone V rearranges to 2-pyridone.

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