通过利用佩塔西斯-费里耶重排的方法,合成 (+) - 博醇A的总合成
A B Smith1, K P Minbiole, P R Verhoest
1Department of Chemistry, Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, PA 19104, USA.
Journal of the American Chemical Society
|November 1, 2001
概括
实现了一种新的 (+) - 福博克萨A的总合成,这是一个强大的抗增殖剂. 这项研究详细介绍了关键的合成策略及其在构建这种复杂分子中的成功应用.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 药用化学 医学化学
背景情况:
- 强效的抗增殖剂 (+) - 博醇A是一种复杂的自然产品.
- 开发有效的合成路径到这些分子对于进一步的生物评估和药物发现至关重要.
研究的目的:
- 为了实现 (+) - 博 A. 的高度融合和立体控制的总合成.
- 探索适用于复杂分子构造的新型合成方法.
主要方法:
- 使用修改后的Petasis-Ferrier重新排列用于cis-tetrahydropyran环组件.
- 采用朱莉烯酸化为乙醇合成,并开发了一种新型的oxazole关键.
- 包含用于最终碎片组装的Stille合器.
主要成果:
- 成功合成 (+) - 博醇A,具有最长的27步线性序列.
- 在总合成中获得3%的整体产量.
- 证明了新型合成策略在复杂分子合成中的实用性.
结论:
- 已经成功地建立了一个高度融合的,立体控制的 (+) - 博醇A的总合成.
- 开发的合成路径展示了关键有机反应的创新应用.
- 这种合成为进一步研究抗增殖剂提供了基础.
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