Epoxidation–cyclization of rosewood oxides

The epoxidation reaction of linalool by MCPBA led to two furanoid oxides (35.7 and 37.0%), known as rosewood oxides, two pyranoid oxides (2.4 and 1.9%) and four rosewood epoxide derivatives. Reaction with BF 3 ‐MeOH of the epoxidized cis ‐furanoid oxide allowed the isolation of a new bicyclic compound [2‐(methoxymethyl)‐1,4,4‐trimethyl‐3,8‐dioxabicyclo(3.2.1)octane], whereas the epoxidized trans ‐furanoid oxide led to a new monocyclic diol methoxy ether [2‐(1‐hydroxy‐2‐methoxyethyl)‐5‐(1‐hydroxy‐1‐methylethyl)‐2‐methyltetrahydrofuran]. 2D‐NMR analyses were used for structure determination. Copyright © 2004 John Wiley & Sons, Ltd.