Banwell Martin G, Gao Nadia Yuqian, Schwartz Brett D, White Lorenzo V
Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.
Top Curr Chem. 2012;309:163-202. doi: 10.1007/128_2011_217.
The total syntheses of a wide range of terrestrially derived alkaloids, especially ones isolated from members of the Amaryllidaceae family, are described. Two recurring themes associated with these syntheses are the use of two types of building blocks, namely ring-fused cyclopropanes, especially geminally-dihalogenated ones, and enzymatically derived cis-1,2-dihydrocatechols. These have often served as precursors to 2- or 3-halogenated 2-cyclohexen-1-ols that are themselves engaged in cross-coupling reactions, radical addition-elimination processes and/or Claisen- or Overman-type rearrangements so as to construct the highly functionalized six-membered rings associated with the target alkaloids.
本文描述了多种源自陆地的生物碱的全合成，特别是从石蒜科植物中分离得到的生物碱。与这些合成相关的两个反复出现的主题是使用两种类型的构建单元，即稠环环丙烷，特别是偕二卤代环丙烷，以及酶促衍生的顺式-1,2-二氢儿茶酚。这些构建单元常常作为2-或3-卤代-2-环己烯-1-醇的前体，而这些醇本身会参与交叉偶联反应、自由基加成-消除过程和/或克莱森重排或奥弗曼重排，从而构建与目标生物碱相关的高度官能化的六元环。
