通过双重化/乳酸化进行 (+) - 化B的总合成
1Department of Chemistry, University of Alberta, Edmonton, AB, T6G 2G2, Canada.
Journal of the American Chemical Society
|January 14, 2010
概括
研究人员首次实现了 (+) - 化乙烯的全合成,化乙烯是来自Ixeris chinensis的天然产品. 这种合成利用了一种新的合性化/乳酸化和环闭转化论,克服了反应性功能组的挑战.
科学领域:
- 自然产品的合成自然产品的合成
- 有机化学 有机化学
- 药用化学 医学化学
背景情况:
- 类化物是瓜伊类型的α-甲基--乳天然产品.
- 这些化合物来自Ixeris chinensis,一种在传统中医中使用的植物.
研究的目的:
- 为了实现B. (+) - 化的第一个enantioselective总合成.
- 为具有反应性部分的复杂天然产品开发高效的合成策略.
主要方法:
- 从 (R) -carvone.开始的酶选择性总合成.
- 关键步骤包括立体选择性和E/Z选择性并列化/乳酸化.
- 化学选择性环闭转化被用来构建七个成员的环.
主要成果:
- 在15个线性步骤中完成了 (+) - 化B的总合成,总产量为6.7%.
- 这种合成成功地解决了与α-甲基烯玛-乳部分相关的化学选择性挑战.
- 开发的方法提供了一条可行的途径,以chinensiolides和相关化合物.
结论:
- 首次对 (+) - 化乙酸的全合成成功完成.
- 这项研究表明,在天然产品合成中,双重化/乳酸化和闭环转化学的实用性.
- 这项工作为含有反应性α-甲基-乳核的分子的合成提供了宝贵的见解.
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