Snider B B, Ahn Y, O'Hare S M
Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Org Lett. 2001 Dec 27;3(26):4217-20. doi: 10.1021/ol016884o.
A 14-step synthesis of martinellic acid (1) that proceeds in 3% overall yield has been completed using the reaction of aniline 11 with Meldrum's acid-activated vinylcyclopropane 4 to give vinyl pyrrolidinone 12, condensation of aldehyde 13 with N-benzylglycine to form an azomethine ylide that cyclizes to give 14, selective reduction of 14 to amino alcohol 16 with LiBH(4) and MeOH, and guanidine formation by reaction of a cyanamide with 3-methyl-2-buten-1-amine in hexafluoro-2-propanol at 120 degrees C as key steps. [structure: see text]
已完成马丁内利酸（1）的14步合成，总产率为3%，该合成使用苯胺11与丙二酸亚异丙酯活化的乙烯基环丙烷4反应生成乙烯基吡咯烷酮12，醛13与N-苄基甘氨酸缩合形成氮杂甲亚胺叶立德，后者环化生成14，用LiBH(4)和甲醇将14选择性还原为氨基醇16，以及在120℃下于六氟-2-丙醇中使氰胺与3-甲基-丁烯-1-胺反应形成胍作为关键步骤。[结构：见原文]
