Access to 3-Prenylated Oxindoles by α-Regioselective Prenylation: Application to the Synthesis of (±)-Debromoflustramine E
Access to 3-Prenylated Oxindoles by α-Regioselective Prenylation: Application to the Synthesis of (±)-Debromoflustramine E
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DOI：
10.1021/acs.orglett.8b00045
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发表时间：
2018-02-16
期刊：
影响因子：
5.2
通讯作者：
Zhao, Li-Ming
中科院分区：
文献类型：
--
作者：
Li, De-Feng;Liu, Kun;Zhao, Li-Ming
描述了使用简单试剂快速、高效、一锅法合成 C3-α-异戊烯基化羟吲哚的方法。该方法基于锌介导的 3-亚酰基-羟吲哚与市售异戊二烯基溴的α-区域选择性异戊二烯化反应，使用廉价的 CeCl3 作为催化剂。新的转化可耐受多种 3-亚酰基-羟吲哚，从而可以轻松获得各种功能化的 3-异戊二烯化羟吲哚。该方法的合成效用通过氟曲明家族生物碱 (+/-)-去溴氟曲明 E 的正式合成得到验证。
The development of a rapid, highly efficient, and one-pot synthesis of C3-alpha-prenylated oxindoles with simple reagents is described. The process is based on zinc-mediated alpha-regioselective prenylation of 3-acylidene-oxindole with commercially available prenyl bromide using inexpensive CeCl3 as the catalyst. The new transformation tolerates a wide range of 3-acylidene-oxindoles, providing easy access to a variety of functionalized 3-prenylated oxindoles. The synthetic utility of the approach is verified by formal synthesis of the flustramine family alkaloid (+/-)-debromoflustramine E.