总合成和绝对立体化学赋值的 (-) -communesin F F
Zhiwei Zuo1, Weiqing Xie, Dawei Ma
1State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Journal of the American Chemical Society
|September 4, 2010
概括
这项研究提出了 (-) -communesin F 的简洁总合成,详细介绍了一种新型的螺旋融合的印度林结构. 研究还成功地分配了天然产品的绝对配置.
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:
- (-) -Communesin F是一种复杂的天然产品,具有独特的螺旋合的印度林核.
- 建立高效的合成路径和确定绝对配置对于理解天然产品的生物活性至关重要.
研究的目的:
- 为了实现 (-) -communesin F. 的简洁不对称的总合成.
- 开发和展示一个前所未有的内部分子氧化合策略,用于螺旋合的Indolines.
- 为了赋予自然 (-) -communesin F. 的绝对配置.
主要方法:
- 不对称的总合成使用TBS保护的 (S) - 基醇作为一种手术辅助剂.
- 甲酸中介的G环形成.
- 通过分子内斯图丁格反应引入A环的后期阶段.
- 新型分子内氧化合用于螺旋合的印烯制备.
主要成果:
- (-) -communesin F的19个步骤合成,总产量约为6%.
- 成功应用了前所未有的分子内氧化合策略.
- 在分子内斯图丁格反应中证明了扭曲胺的增强反应性.
- 在F中自然公社的绝对配置的赋值为6R,7R,8R,9S,11R.
结论:
- 开发的合成路线简洁而有效,用于访问F的 (-) -communesin F.
- 新的氧化合策略是有效的,用于构建螺旋合的印度林部分.
- 这项研究为扭曲胺基的反应性提供了宝贵的见解,并证实了F. communesin中社区的绝对配置.
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