Preparation of (R)-(+)-3-phenyl-2,3,5,6,7,8-hexahydrooxazolo-[3,2-a]pyridin-4-ylium bromide:: Synthesis of (S)-(+)-coniine, (R)-(-)-coniceine and (R)-(+)-anabasine
Preparation of (R)-(+)-3-phenyl-2,3,5,6,7,8-hexahydrooxazolo-[3,2-a]pyridin-4-ylium bromide:: Synthesis of (S)-(+)-coniine, (R)-(-)-coniceine and (R)-(+)-anabasine
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DOI：
10.1016/s0385-5414(07)81205-6
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发表时间：
2007-12-01
期刊：
影响因子：
0.6
通讯作者：
Gnecco, Dino
中科院分区：
文献类型：
--
作者：
Castro, Alejandro;Ramirez, Johana;Gnecco, Dino
我们描述了用POBr3将(R)-(-)-1-(2‘-hydroxy-1’-phenylethyl)piperidin-2-one 1转化为(R)-(-)-3-phenyl-2，3，5，6，7，8-hexahydro-oxazolo[3，2-a]pyridin-4-ylium溴化物2，在-78℃用红铝还原2得到(3R，8aR)-(-)-3-phenylbexahydro-2H-oxazolo[3，8-a]-pyridine 3作为单一的非对映异构体。这些转化的合成潜力通过(S)-(+)-刀豆碱、(R)-(-)-刀豆碱和(R)-(+)-花椒碱的对映体合成来说明。
We describe the transformation of (R)-(-)-1-(2'-hydroxy-1'-phenylethyl)piperidin-2-one 1 into (R)-(-)-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium bromide 2 using POBr3, Reduction of 2 with Red-Al at -78 degrees C gave (3R,8aR)-(-)-3-phenylbexahydro-2H-oxazolo[3,8-a]-pyridine 3 as a single diastereoisomer. The synthetic potential of these transformation is illustrated by the enantiopure synthesis of (S)-(+)-coniine, (R)-(-)-coniceine and (R)-(+)-anabasine.