Tetrahydrofurans cerium ammonium nitrate

One-electron oxidation of the p-allyloxy nitroalkane (85) by cerium ammonium nitrate (CAN) produces a tetrahydrofuran derivative (86) (eq. 3.31). 

Cerium(IV) ammonium nitrate in aqueous acetonitrile will also cleave a p-methoxyp/zeny/ ether (presumably to benzoquinone).335 The reaction was used in a synthesis of Stigmastellin A [Scheme 4.183] to release a primary alcohol in the presence of a benzyl ether.339 In an extension of the method, a bidirectional strategy for the synthesis of 2,3 5-trisubstitute d tetrahydrofuran components of annonaceous acetogenins benefited from the simultaneous protection of two primary hydroxyls as their Cj-symmetric hydroquinone ether [Scheme 4.184].340... 

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