Total synthesis of (-)-cassine.
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]
Makabe
Hidefumi
H
Graduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-minowa Kami-ina, Nagano 399-4598, Japan. makabeh@gipmc.shinshu-u.ac.jp
Kong
Looi Kok
LK
Hirota
Mitsuru
M
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002366:Cassia / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis*
D000470:Alkaloids; D007659:Ketones; D010880:Piperidines; C426663:cassine