The first enantioselective total synthesis of (+)-preussin B and an improved synthesis of (+)-preussin by step-economical methods

The first enantioselective total synthesis of (+)-preussin B and an improved synthesis of (+)-preussin by step-economical methods
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首次对映选择性全合成 ( )-preussin B 以及通过分步经济方法改进合成 ( )-preussin

DOI:
10.1007/s11426-014-5270-0
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发表时间:
2015-01
期刊:
Science China Chemistry
影响因子:
--
通讯作者:
Xiao Kai-Jiong
Xiao Kai-Jiong
中科院分区:
其他
文献类型:
--
作者:
Huang Pei-Qiang;Geng Hui;Tian Yong-Song;Peng Qiu-Ran;Xiao Kai-Jiong

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报道了(+)-普鲁辛B的首次对映选择性全合成和抗真菌生物碱(+)-普鲁辛的改进合成。我们的方法依赖于我们实验室开发的四步经济的合成方法:(1)半缩醛的非对映选择性还原脱羟基;(2)直接酰胺/内酰胺还原烷基化;(3)一锅N,O-双脱苄基-N-甲基化;(4)由苹果酸一步合成马来酰亚胺。这两种全合成方法都很简洁,均由六步完成,总收率分别为25.7%和27.6%。
The first enantioselective total synthesis of (+)-preussin B and an improved synthesis of the antifungal alkaloid (+)-preussin are described. Our approach relied on the four step-economical synthetic methods developed in our laboratory: (1) thecis-diastereoselective reductive dehydroxylation of hemiaminals; (2) the direct amide/lactam reductive alkylation; (3) the one-potN,O-bisdebenzylation-N-methylation; and (4) the one-step synthesis of malimide from malic acid. Both total syntheses are quite concise, which have been achieved in six steps, and gave overall yields of 25.7% and 27.6%, respectively.
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发表时间: 2012-09
影响因子: 2.5
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