高等学校化学学报

高等学校化学学报 ›› 1995, Vol. 16 ›› Issue (12): 1914.

• 研究简报 • 上一篇    下一篇

吡咯烷生物碱及相关化合物的不对称合成研究(Ⅰ)

黄培强, 阮源萍   

  1. 厦门大学化学系, 厦门, 361005
  • 收稿日期:1995-02-09 修回日期:1995-05-20 出版日期:1995-12-24 发布日期:1995-12-24
  • 通讯作者: 黄培强,男,33岁,博士,研究员.
  • 作者简介:黄培强,男,33岁,博士,研究员.
  • 基金资助:

    国家教委霍英东教育基金;国家自然科学基金

Studies on the Asymmetric Synthesis of Pyrrolidine Alkaioids and Related Compounds(Ⅰ)──Synthesis or a Chiral Precursor for Preussin and AHPPA

HUANG Pei-Qiang, RUAN Yuan-Ping   

  1. Department of Chemistry, Xiamen University, Xiamen, 361005
  • Received:1995-02-09 Revised:1995-05-20 Online:1995-12-24 Published:1995-12-24

PDF (PC)

被引次数

4

关键词: Preussin, 4-氨基-3-羟基-5-苯基戊酸, 不对称合成, 酰胺-&alpha, -烷基化, 1, 5-二苄基-4-苄氧基-2-吡咯酮

Abstract: Starting from(S)-malic aicd, the stereoselective synthesis of(4S, 5R)-1,5-dibenzyl-4-benzyloxyl-2-pyrrolidone 9 by two methods was described.The key steps in the synthesis are two asymmetric α-amidoalkylation.The asymmetric α-amidoalkylation was easily achieved either from sulfone 7by Ley's method or from 5 via an addition-reduction proceed to provide 9 in good(4/1 for 7) to excellent(97/3 for 5)trans stereoselectivity.Compound 9 is a chiral precursor for(-)-preussin and(3S,4R )-4-amino-3-hydroxyl-5-phenylpentanoic acid(AHPPA).

Key words: Preussin, 4-Amino-3-hydroxyl-5-phenylpentanoic acid, Asymmetric synthesis, α-Amidoalkylation, 1,5-Dibenzyl-4-benzyloxyl-2-pyrrolidone

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