New route to the ergoline skeleton via cyclization of 4-unsubstituted indoles.
New route to the ergoline skeleton via cyclization of 4-unsubstituted indoles.
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DOI：
10.1021/ol400620a
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发表时间：
2013-05
期刊：
影响因子：
5.2
通讯作者：
Scott D. Burley;Vicky V. Lam;F. Lakner;B. Bergdahl;M. Parker
中科院分区：
文献类型：
--
作者：
Scott D. Burley;Vicky V. Lam;F. Lakner;B. Bergdahl;M. Parker
已经开发了一种新的麦角林骨架路线，其不需要吲哚4-位的预先官能化。吲哚核在合成后期引入，以允许在该区域中最终有效地引入取代基。关键步骤包括Negishi偶联的三碳链的溴烟酸酯，Fischer吲哚合成，以促进取代基通过苯肼，Pd催化的环化反应，形成麦角林C环。
A new route to the ergoline skeleton has been developed that does not require prior functionalization of the indole 4-position. The indole nucleus is introduced late in the synthesis to allow for eventual efficient introduction of substituents in this region. Key steps include Negishi coupling of a three-carbon chain to a bromonicotinate ester, Fischer indole synthesis to facilitate incorporation of substituents via phenylhydrazines, and Pd-catalyzed cyclization to form the ergoline C ring.