Department of Chemistry, Indiana University , Bloomington, Indiana 47405, United States.
Org Lett. 2014 Apr 4;16(7):1956-9. doi: 10.1021/ol5005092. Epub 2014 Mar 27.
An enantiocontrolled synthesis pathway has been developed to provide formation of tricyclic amine 7, representing the ABC ring system of the complex alkaloid daphnicyclidin A (1). Our efforts describe preparation of the Z-hexahydro-(1H)-azocine 29 and cyclization to construct the novel 4-azabicyclo[5.3.2]dodecane 31. Transannular reductive amination following the deprotection of 31 gave the desired tertiary amine 7.
已开发出一种对映选择性合成途径，以提供三环胺 7 的形成，该三环胺代表复杂生物碱 daphnicyclidin A（1）的 ABC 环系统。我们的努力描述了 Z-六氢-（1H）-氮杂环辛烷 29 的制备和环化以构建新型 4-氮杂双环[5.3.2]十二烷 31。31 的脱保护后进行反式环还原胺化，得到所需的叔胺 7。
