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总合成和绝对立体化学赋值的 (+) - 和 (-) - 加尔布利米玛化物13
Mohammad Movassaghi1, Diana K Hunt, Meiliana Tjandra
1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA. movassag@mit.edu
Journal of the American Chemical Society
|June 22, 2006
概括
这项研究详细介绍了galbulimima化物13的总合成,修订了它的立体化学和建立了一个新的合成路径. 这项研究提供了一种可靠的方法来构建复杂的五环类化物结构.
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:
- 加尔布利米玛类化合物是一个复杂的自然产品类别,具有潜在的生物活性.
- 由于它们复杂的五环结构,这些类化合物的总合成存在重大挑战.
研究的目的:
- 为了实现 (+) - 和 (-) - 白胺类化合物的总合成13.
- 修订天然 (-) - - 白胺类化合物的绝对立体化学 13.
- 开发一个复杂的galbulimima类化合物的可通用合成策略.
主要方法:
- 连续的催化交叉合和交叉转化反应.
- 内分子迪尔斯-阿尔德反应用于跨十林AB环系统的构造.
- 乙烯基基的激素循环化用于C环的形成.
- 从N-乙烯基碳酸盐中揭示C16的后期阶段.
主要成果:
- 13.成功合成了两种galbulimima类化合物的双反体.
- 对天然 (-) - - 白胺类化合物13至2S的绝对立体化学的修订.
- 五环芯的高效构造,具有完整的二选择.
- 展示了引入CDE环系统的战略.
结论:
- 开发的合成策略是有效的构建复杂的galbulimima类化合物.
- 修订后的立体化学提供了关键信息,以了解这种类化合物的结构-活性关系.
- 这项工作为合成其他相关的自然产品开辟了道路.
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