Total synthesis of (+/-)fasicularin via a 2-amidoacrolein cycloaddition.
Total synthesis of (+/-)fasicularin via a 2-amidoacrolein cycloaddition.
复制标题
通过 2-酰胺丙烯醛环加成全合成 (i-)fasillaryin。
DOI：
10.1021/ol016850g
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发表时间：
2002
期刊：
影响因子：
5.2
通讯作者：
Funk,RaymondL
中科院分区：
文献类型：
--
作者：
Maeng,Jun-Ho;Funk,RaymondL
The total synthesis of the cytotoxin fasicularin is described. The key steps include the following: (1) an intermolecular Diels−Alder cycloaddition of a 2-(triflamido)acrolein with the dioxolane ketal of trideca-1,3-dien-7-one to establish thetrans-perhydroisoquinoline stereochemistry, (2) a stereoelectronically controlled hydride addition to a N(1)−C(2) iminium ion to introduce the equatorial hexyl substituent, and (3) elaboration of the pyrido ring by an internal aldol reaction.
