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化学学报
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化学学报 ›› 1992, Vol. 50 ›› Issue (9): 901-904. 上一篇    下一篇

研究论文

番荔枝皂素(4S,5S)和(4S,5R)-Muricatacin的合成及Annonacin四氢呋喃段绝对构型的确证

姚祝军;张一兵;吴毓林   

  1. 中国科学院上海有机化学研究所;中国科学院生命有机化学国家重点实验室
  • 发布日期:1992-09-15

Synthesis of annonaceous acetogenin (4S,5S) and (4S,5R)-muricatacin as well as confirmation of absolute configuration of the tetrahydrofuran segment of annonacin

YAO ZHUJUN;ZHANG YIBING;WU YULIN   

  • Published:1992-09-15

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469

被引次数

1

本文以L-谷氨酸为原料合成了(1S,5S)和(4S,5R)-Muricatacin,并以该两化合物的NMR和[a]~D数据确证了Annonacin中四氢呋喃段的四个手性中心为(15R,16R,19R,20R).

关键词: 核磁共振谱法, 还原, 谷氨酸, 四氢呋喃 P, 绝对构型, 番荔枝皂素

The synthesis of (+)-(4S,5S)-muricatacin (I) and its (4S,5R) isomer from L-(+)-glutamic acid as starting material is reported. Natural muricatacin is confirmed as a threo mixture major in (4R,5R) configuration and hence the absolute configuration of the THF segment of annonacin is (15R,16R,19R,20R) by comparison of the NMR and optical rotations.

Key words: NMR SPECTROMETRY, REDUCTION, GLUTAMIC ACID, TETRAHYDROFURAN P, ABSOLUTE CONFIGURATION

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