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Atroposelective Total Syntheses of Naphthylisoquinoline Alkaloids with (P)-Configuration.
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2020-09-14 , DOI: 10.1021/acs.joc.0c01661
Young-In Jo 1 , Chun-Young Lee 1 , Cheol-Hong Cheon 1
Affiliation  

Asymmetric total syntheses of naphthylisoquinoline alkaloids with a (P)-configuration are described. An atroposelective Suzuki–Miyaura reaction between naphthyl pinacol boronate and an aryl iodide bearing an (S)-2-(N-acetylamino)propyl group at the ortho-position using Pd(OAc)2 in the presence of SPhos and Ba(OH)2 provided the (P)-selective biaryl product as the major product without any external chiral sources. This biaryl product was converted into naphthylisoquinoline alkaloids with a (P)-configuration via stereoselective construction of the isoquinoline framework with the appropriate oxidation state and stereochemistry.

中文翻译:

具有(P)-构型的萘基异喹啉生物碱的Atroposelective总合成。

描述了具有(P)构型的萘基异喹啉生物碱的不对称全合成。在SPhos和Ba(OH)存在下,使用Pd(OAc)2位带有萘酚萘酚萘甲酸硼酸酯和带有位带(S)-2-(N-乙酰氨基氨基)丙基的芳基碘化物之间的对映选择性Suzuki-Miyaura反应图2提供了(P)-选择性联芳基产物作为主要产物,而没有任何外部手性来源。经由具有适当氧化态和立体化学的异喹啉骨架的立体选择性构建,将该联芳基产物转化为具有(P)构型的萘基异喹啉生物碱。
更新日期:2020-10-02
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