R e a g e n t f o r t h e S y n t h e s i s o f T e r t i a r y E t h e r sAbstract: Treatment of tertiary 1,4-and 1,5-diols with cerium ammonium nitrate at room temperature led to the corresponding tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Utilizing this methodology, manoyl oxide (25a) and a variety of fragrant compounds, such as linalool oxide (8), caparrapi oxide (12), ambrox (14) and other related amber-gris-type odorants have been synthesized; 16 examples are described.
2006 Pyran derivatives R 0340 Cerium(IV) Ammonium Nitrate (CAN): A Very Efficient Reagent for the Synthesis of Tertiary Ethers. -The process is suitable for the preparation of various terpenes (fragrant substances) and affords the higher systems in most cases with complete diastereoselectivity. -(ALVAREZ-MANZANEDA*, E. J.; CHABOUN, R.; ALVAREZ, E.; CABRERA, E.; ALVAREZ-MANZANEDA, R.; HAIDOUR, A.; RAMOS,
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