罗斯菲林的合成和绝对立体化学
1Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, HI 96822, USA.
Journal of the American Chemical Society
|August 30, 2001
概括
实现了天然素的总合成,确定了它的绝对配置. 这项研究促进了对复杂的天然产品合成和立体化学的理解.
科学领域:
- 有机化学 有机化学
- 自然产品的合成自然产品的合成
- 立体化学是一种立体化学.
背景情况:
- 素是一种复杂的天然产品,具有显著的生物活性.
- 确定自然产品的绝对配置对于理解它们的功能至关重要.
- 以前的合成路线可能在效率或立体控制方面存在局限性.
研究的目的:
- 为了实现第一个天然色素的enantiospecific总合成.
- 确定素的绝对配置为22R,23R.
- 开发一种高效的合成策略,采用不对称的环.
主要方法:
- 一个特定的总合成策略.
- 作为一个关键步骤的不对称环化反应.
- 基拉尔染色学用于反体过量测定.
主要成果:
- 罗斯菲林的总合成在15个步骤中完成,总产量为7.0%.
- 自然产品的绝对配置被证实为22R,23R.
- 一个关键的中间体,环二烯 (+) - 12,在78%的产量和86%的反体过剩 (ee) 中进行了合成.
结论:
- 成功的酶特异合成验证了拟议的合成路径.
- 这项工作提供了一种可靠的方法来获取roseophilin及其类似物.
- 建立的绝对配置为未来的研究提供了最终的参考.
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