Phenol Dehydrogenations. 13. Structure of "Cedrone" - Spectral Evidence.

Biomimetic Synthesis of the Calcineurin Phosphatase Inhibitor Dibefurin

“…Reactions of this type have been previously observed with simple and symmetric pyrogallol and phloroglucinol derivatives. [19] Exposing epicoccine to ortho-chloranil or DDQ failed to yield dibefurin (entries 1, 2). However, the use of excess FrØmy's salt afforded our target compound in modest yield (entry 3).…”

The crystal and molecular structure of symmetrical cedrone, a dimeric oxidation product of trimethylphloroglucinol

“…Cedrone, made according to the directions of Erdtman (1934), separated from DMF solution as a solvate in the form of colorless monoclinic prisms. Precession photographs determined the space group uniquely as P2ffc; systematic absences: 0k0 absent with k odd and hOl absent with 1 odd.…”

“…In the following year Cecelsky (1899), during the course of a reinvestigation of the reaction, named the product 'cedrone' because its hydrogen iodide reduction product had the odor of cedar wood. Many years later Erdtman (1934) proposed a dimeric structure (I) for cedrone OH OH (I) which he revised in 1969 (Erdtman, Moussa & Nielsson, 1969) on the basis of results from analogous work and with the benefit of spectroscopic analysis of both cedrone and its derived acetates and methyl ethers. He concluded that the structure of cedrone could be represented by a pair of bis-enol dimeric structures: a 'symmetric' form (IIa) and an 'unsymmetric' form (IIb).…”