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The structurally intriguing terpenes pallambins C and D have been assembled in only 11 steps from a cheap commodity chemical: furfuryl alcohol. This synthesis, which features a redox-economic approach free of protecting-group manipulations, assembles all four-ring systems via a sequential cyclization strategy. Of these fourring constructing operations, two are classical (Robinson annulation and Mukaiyama aldol) and two are newly devised. During the course of this work a method for the difunctionalization of enol ethers was developed, and the scope of this transformation was explored. [ABSTRACT FROM AUTHOR]

3-Carene, α-pinene, and limonene α-(dimethylamino)oximes were converted to glycidyl ethers at the oxime hydroxyl. The compounds obtained were involved in the reactions with amines, imidazole, as well as with anions of these dimethylamino oximes. The glycidyl ether epoxide ring opening by amines under microwave irradiation conditions proceeds considerably faster than upon convection heating. [ABSTRACT FROM AUTHOR]