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Synthesis of 3-azabicyclo[3.3.0]octane framework and a novel tricyclicaminoether

2003-01-01
Kaniskan, HU
Doğan, Özdemir
The efficient synthesis of 3-azabicyclo[3.3.0]octane derivative 1 and a novel tricyclicaminoether 11 has been achieved in seven steps using commercially available starting materials and commonly used reagents. The key steps are the intramolecular ring opening of epoxide 7 providing tricyclic aminoalcohol 3 and Baeyer-Villiger oxidation of ketone 8 providing the corresponding lactone 2. Both reactions proceeded regiospecifically.