通过氮杂环丙烷的 5-endo-环化形成四氢呋喃——(-)-巴卡亭 III 的合成。
Formation of tetrahydrofurans via a 5-endo-tet cyclization of aziridines--synthesis of (-)-pachastrissamine.
机构信息
Department of Chemistry, National Central University, 300 Jhong-Da Road, Jhong-Li, Taoyuan, Taiwan.
出版信息
Org Biomol Chem. 2013 Aug 28;11(32):5292-9. doi: 10.1039/c3ob40797g.
The formation of tetrahydrofurans from 2-hydroxyalkyl-oxirane or aziridine is reported. The 5-endo-tet cyclization/ring opening of aziridine proceeded smoothly to give tetrahydrofurans (THFs) under mild conditions. In contrast, the corresponding process of oxirane was unsuccessful and a sequence of SN2 substitution/cyclization was required to form THFs. The application of the process to prepare ent-(-)-pachastrissamine is described.
报告了 2-羟烷基-环氧乙烷或氮杂环丙烷转化为四氢呋喃（THF）的反应。氮杂环丙烷的 5-endo-四元环化/开环反应在温和条件下顺利进行，得到了四氢呋喃（THF）。相比之下，相应的环氧乙烷过程并不成功，需要经历 SN2 取代/环化反应序列才能形成 THF。描述了该过程在制备 (-)-pachastrissamine 的应用。
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