Martinez M Montserrat, Hoppe Dieter
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, D-48149 Münster, Germany.
Org Lett. 2004 Oct 14;6(21):3743-6. doi: 10.1021/ol0485666.
[reaction: see text] We report a new enantioselective synthesis of (-)-alpha-kainic acid from d-serine methyl ester hydrochloride, based on a (-)-sparteine-mediated asymmetric deprotonation of an intermediate carbamate that, by stereospecific anti S(N)'S(E)' intramolecular cycloalkylation, leads to the pyrrolidine ring precursor of (-)-alpha-kainic acid, in high yield and diastereoselectivity. The intermediate pyrrolidine was further transformed to (-)-alpha-kainic acid in three steps.
[反应：见正文] 我们报道了一种从D-丝氨酸甲酯盐酸盐出发，以（-）-鹰爪豆碱介导的中间体氨基甲酸酯的不对称去质子化反应为基础的（-）-α-红藻氨酸的新对映选择性合成方法。该反应通过立体专一性的反式S(N)'S(E)'分子内环烷基化反应，以高收率和非对映选择性得到（-）-α-红藻氨酸的吡咯烷环前体。中间体吡咯烷经三步反应进一步转化为（-）-α-红藻氨酸。
