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The Hancock Alkaloids (-)-Cuspareine, (-)-Galipinine, (-)-Galipeine, and (-)-Angustureine: Asymmetric Syntheses and Corrected 1H and 13C NMR Data.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2018-11-20 , DOI: 10.1021/acs.jnatprod.8b00672
Stephen G Davies 1 , Ai M Fletcher 1 , Ian T T Houlsby 1 , Paul M Roberts 1 , James E Thomson 1 , David Zimmer 1
Affiliation  

The asymmetric syntheses of all members of the Hancock alkaloid family based upon a 2-substituted N-methyl-1,2,3,4-tetrahydroquinoline core are delineated. The conjugate addition of enantiopure lithium N-benzyl- N-(α-methyl- p-methoxybenzyl)amide to 5-( o-bromophenyl)- N-methoxy- N-methylpent-2-enamide is used to generate the requisite C-2 stereogenic center of the targets, while an intramolecular Buchwald-Hartwig coupling is used to form the 1,2,3,4-tetrahydroquinoline ring. Late-stage diversification completes construction of the C-2 side chains. Thus, (-)-cuspareine, (-)-galipinine, (-)-galipeine, and (-)-angustureine were prepared in overall yields of 30%, 28%, 15%, and 39%, respectively, in nine steps from commercially available 3-( o-bromophenyl)propanoic acid in all cases. Unambiguously corrected 1H and 13C NMR data for the originally isolated samples of (-)-cuspareine, (-)-galipinine, and (-)-angustureine are also reported, representing a valuable reference resource for these popular synthetic targets.

中文翻译:

汉考克生物碱(-)-Cuspareine,(-)-Galipinine,(-)-Galipeine和(-)-Angustureine:不对称合成以及校正后的1H和13C NMR数据。

描绘了基于2-取代的N-甲基-1,2,3,4-四氢喹啉核心的汉考克生物碱家族的所有成员的不对称合成。将对映体纯的N-苄基锂-N-(α-甲基-对甲氧基苄基)酰胺共轭添加到5-(邻溴苯基)-N-甲氧基-N-甲基戊-2-烯酰胺中以生成必要的C- 2立体定向的目标,而分子内布赫瓦尔德-哈特维格偶联是用来形成1,2,3,4-四氢喹啉环。后期多样化完成了C-2侧链的构建。因此,分九步制备(-)-cuspareine,(-)-galipinine,(-)-galipeine和(-)-angustureine的总产率分别为30%,28%,15%和39%在所有情况下均由市售的3-(邻-溴苯基)丙酸制成。
更新日期:2018-11-20
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