立体选择性氮宾离子介导的环官能化反应：（+）-castanospermine 的全合成。
Diastereoselective nitrenium ion-mediated cyclofunctionalization: total synthesis of (+)-castanospermine.
机构信息
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.
出版信息
Org Lett. 2010 Nov 19;12(22):5330-3. doi: 10.1021/ol102371x. Epub 2010 Oct 21.
Abstract
The asymmetric total synthesis of the α-glucosidase inhibitor (+)-castanospermine is reported. The central theme in our approach to this polyhydroxylated alkaloid is the simultaneous generation of the piperidine ring and the C-1/8a erythro stereodiad through the diastereoselective, oxamidation of an unsaturated O-alkyl hydroxamate. This process is believed to proceed sequentially via singlet acylnitrenium and aziridinium ion intermediates.
摘要
本文报道了α-葡萄糖苷酶抑制剂（+）-castanospermine 的不对称全合成。我们对这种多羟基生物碱的方法的中心主题是通过不饱和 O-烷基羟肟酸的非对映选择性氧化酰胺化，同时生成哌啶环和 C-1/8a 赤立体二氢嘧啶。这个过程被认为是通过单重态酰基氮宾和氮丙啶离子中间体顺序进行的。
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