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| LETTER | Synlett 2006: 1829-1834
DOI: 10.1055/s-2006-947356 |
© Georg Thieme Verlag Stuttgart · New York
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Cerium(IV) Ammonium Nitrate (CAN): A Very Efficient Reagent for the Synthesis of Tertiary Ethers
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| E. J. Alvarez-Manzaneda*a, R. Chabouna, E. Alvareza, E. Cabreraa, R. Alvarez-Manzanedab, A. Haidoura, J. M. Ramosa |
a Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain, +34(958)248089
e-Mail: eamr@ugr.es;
b Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Almería, 04120 Almería, Spain
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Received
14 March 2006 |
Abstract
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. Key words
cyclizations - diols - ethers - natural products - stereoselectivity
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