类立体控制的 (-) - 巨乳素 A 的合成
Joseph P Marino1, Michael S McClure, David P Holub
1Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Journal of the American Chemical Society
|February 21, 2002
概括
综合 (-) - - 巨乳素A,一个复杂的化物,通过新的方法实现了整体合成,用于立体中心的引入. 关键步骤包括不对称的减少,性硫氧化物化学和特定的精技术.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 自然产品的合成自然产品的合成
背景情况:
- (-) - - 麦克罗拉克丁A是一种具有显著生物学意义的24个成员的化物.
- 复杂宏类的总合成带来了相当大的立体化学挑战.
- 以前的合成路线可能缺乏效率或立体选择性.
研究的目的:
- 为了实现第一个 (-) - 巨乳素A的全合成,A.
- 开发和应用新的合成方法来构建宏核.
- 通过使用新的1,3-二醇合成,有效地引入两个关键的立体性中心.
主要方法:
- 开发了一种新的1,3-二醇合成.
- 序列的诺约里不对称的减少和性硫氧化物方法.
- 用于C8 Z/E-diene装置的提衍生铜酸有机金属.
- 朱莉亚-莱斯戈为C15E/E段结构的精细化.
- 山口乳化用于宏循环形成.
主要成果:
- 成功完成了 (-) - 巨乳素A的总合成.
- 通过1,3-二醇合成,有效地引入两个立体中心.
- 在C8二烯和C15段的高度立体选择性安装.
- 采用了收合成策略.
结论:
- 开发的合成策略提供了一个有效的途径,以 (-) - 巨乳素A.
- 新的1,3-二醇合成子是引入立体中心的宝贵工具.
- 合成突出了现代有机金属和精反应在复杂分子结构中的力量.
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