高等学校化学学报

高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (5): 737.

• 论文 • 上一篇    下一篇

包公藤甲素全合成的研究(Ⅱ)——中间体8-甲基-2β-羟基-8-氮二环[3.2.1]辛烷-6-exo-腈的合成

曾陇梅, 杨善淼, 苏镜娱, 吴建青, 万一千   

  1. 中山大学化学系, 广州, 510275
  • 收稿日期:1997-04-05 出版日期:1998-05-24 发布日期:1998-05-24
  • 通讯作者: 苏镜娱
  • 作者简介:曾陇梅,男,66岁,教授.
  • 基金资助:

    国家自然科学基金;广东省自然科学基金

Studies on the Total Synthesis of Natural Alkaloid 6-exo-(Acetyoxy)-8-azabicyclo [3.2.1] octan-2-exo-ol (Ⅱ)——The Synthesis of an Intermediate, 8-Methyl-2β-hydroxy-8-azabicyclo [3.2.1] octane-6-exo carbonitrile

ZENG Long-Mei, YANG Shan-Miao, SU Jing-Yu, WU Jian-Qing, WAN Yi-Qian   

  1. Department of Chemistry, Zhongshan University, Guangzhou, 510275
  • Received:1997-04-05 Online:1998-05-24 Published:1998-05-24

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摘要： 研究了N-甲基-3-羟基吡啶锚盐与丙烯腈的1,3-偶极环加成反应.由环合产物经过氢化,还原得包公藤甲素的中间体8-甲基-2β-羟基-8-氮二环[3.2.1]辛烷-6-exo-腈.本合成路线具有高立体选择性.

关键词: 包公藤甲素, 1, 3-偶极环加成, 合成, 8-甲基-2&beta, -羟基-8-氮二环[3.2.1]辛烷-6-exo-腈

Abstract: The reaction of N-methyl-3-hydroxypyridinium iodide with acrylonitrile has been studied. Under various reaction conditions, none of the desired cycloaddition product was resulted. Instead, a Michael addition product was obtained. Alternatively, the 1,3-dipolar cycloaddition was achieved by the reaction of N-methyl-3-oxopyridinium betaine with acrylonitrile in THF with a high regioselectivity and stereoselectivity. This paper reports the synthesis of an intermediate 8-methyl-2-β-hydroxy-8-azabicyclo [3.2.1] octane-6-exo-carbonitrile of 6-exo-(acetyoxy)-8-azabicyclo [3.2.1]-octan-2-exo-ol. This synthetic route involves two high stereoselective steps.

Key words: 6-exo-(Acetyoxy)-8-azabicyclo[3.2.1]-octan-2-exo-ol, 1,3-Dipolar cycloaddition, Synthesis, 8-Methyl-2-β-hydroxy-8-azabicyclo[3.2.1]octane-6-exo-carbonitrile

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