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2520178

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2001
alkaloids
U 0600
02 - 217
alkaloids
An Alternative Improved Synthesis of (-)-Norferruginine, a Potent
nAChR Agonist.
— An alternative asymmetric synthesis of the title
compound (IX) is achieved in 44% overall yield from cocaine hydrochloride (I)
via the enantiomerically pure tropinone (II) as key intermediate. The acetyl
side chain is introduced in masked form by reaction of the enol triflate (VI)
with ethyl vinyl ether (VII) under Heck conditions. The enol triflate (VI) is
not only an ideal starting material for the introduction of the acetyl side chain
but also a possible precursor for the synthesis of a variety of ferruginine analogues. — (WEGGE, T.; SCHWARZ, S.; SEITZ, G.; Pharmazie 55 (2000) 10,
779-780; Inst. Pharm. Chem., Philipps-Univ., D-35037 Marburg, Germany; EN)
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