801294-25-7Relevant articles and documents
Synthesis and some transformations of (-)-carveol
Valeev,Vostrikov,Miftakhov
experimental part, p. 810 - 814 (2009/12/09)
Reduction of the oxo group in (-)-carvone with LiAlH4, NaBH4, and (i-Bu)2AlH was performed. It was found that the reduction with the system CeCl3 ? 7 H2O-NaBH4 in methanol at 20°C is the most practical procedure for the synthesis of (-)-carveol. Solvolysis of (-)-carvyl methanesulfonate gave products of SN2 and SN2' replacement of the methylsulfonyloxy group, the latter slightly prevailing. Overman rearrangement of (-)-carveol resulted in the formation of the corresponding trichloroacetamide derivative, and intramolecular iodoetherification of the title compound afforded 6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene. Pleiades Publishing, Ltd., 2009.