Organic Letters 2003-Jan
Total synthesis of (-)-cassine.
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Abstrè
The PdCl(2)-catalyzed cyclization of amino allylic alcohol 16 gave the cyclized product 17a with excellent diastereoselectivity. The versatility of compound 17a as the building block for synthesizing cis-2,6-disubstituted piperidine alkaloids has been demonstrated by a total synthesis of (-)-cassine (1). [reaction--see text]