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Two diastereomeric huprines additionally functionalized at position 13 with a methanesulfonamido group have been synthesized in seven steps from the known 9,9-ethylenedioxybicyclo[3.3.1]nonane-3,7-dione (5). In a key-step, nickel boride non-stereoselective reduction of an oxime gave a mixture of amines which was separated as methanesulfonamido derivatives. The substitution pattern of these huprines...
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