实用对映选择性合成保护的 1,4-反式-1,5-顺式-4,5-二氨基-2-环戊烯-1-醇衍生物。
Practical enantiospecific synthesis of an orthogonally protected 1,4-trans-1,5-cis- 4,5-diamino-2-cyclopenten-1-ol derivative.
机构信息
Shanghai Boramino Chemicals Co., Ltd., Room 202, Unit 5, Building 1, 688 Qiushi Road, Shanghai 201512, China.
出版信息
J Org Chem. 2010 Sep 3;75(17):6012-5. doi: 10.1021/jo1009118.
PMID:20690776
Abstract
An enantiospecific synthesis of an orthogonally protected 1,4-trans-1,5-cis-4,5-diamino-2-cyclopenten-1-ol derivative 16 is reported. The trans-diamine moiety was established by anti-specific vinyl addition to a novel threitol-derived tert-butanesulfinylimine 2 and Overman rearrangement. The cyclopentene skeleton was constructed via RCM reaction of a key 1,6-diene intermediate 11.
摘要
报告了一种对映体特异性合成的邻位保护的 1,4-反式-1,5-顺式-4,5-二氨基-2-环戊烯-1-醇衍生物 16。反式二胺部分通过新型苏糖醇衍生的叔丁基亚磺酰亚胺 2 的反位特异性乙烯基加成和 Overman 重排反应来构建。环戊烯骨架是通过关键的 1,6-二烯中间体 11 的 RCM 反应构建的。
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