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 degrees 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).
De
Saroj R
SR
Department of Chemistry, Indian Institute of Technology, Kharagpur, India 721302.
Ghorai
Sujit K
SK
Mal
Dipakranjan
D