来自Cyrene的 (+) -majoranolide的实用和可扩展的反选择性合成
Harald Podversnik1, Jason E Camp2, Ben W Greatrex1
1Faculty of Medicine and Health, University of New England, Armidale, NSW, 2351, Australia. ben.greatrex@une.edu.au.
Organic & biomolecular chemistry
|January 11, 2024
概括
研究人员实现了Persea-derived γ-lactones, (+) -majoranolide和 (+) -majoranolide B. 的格拉姆级合成. 这种新的方法,使用Cyrene和化物,也证实了这些天然产品的绝对配置.
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
背景情况:
- γ-乳酸盐是一种在自然界中发现的一类有机化合物.
- 基利丁 γ-乳酸盐,如 (+) - 巨化和 (+) - 巨化B,是来自Persea属的.
- 这些天然产品的合成和绝对配置的确定具有重大意义.
研究的目的:
- 开发一个可扩展和enantioselective合成 (+) -majoranolide和 (+) -majoranolide B. 的.
- 通过合成和与光学旋转数据的比较,确定这些自然产品的绝对配置.
- 报告这些特定的化天然产品的首次合成.
主要方法:
- 采用了一种两步合成序列.
- 第一个步骤涉及Cyrene (一种生物可再生的synthon) 和亚利法性化物之间的氨基促进交叉凝结.
- 第二个步骤是贝耶-维利格氧化.
主要成果:
- 一个 (+) - 巨化物和 (+) - 巨化物B的格拉姆尺度成功合成了enantioselectively.
- 对光学旋转数据的比较证实了天然产品系列的绝对配置.
- 这项研究是首次报告这些基烯天然产品的合成.
结论:
- 已经建立了一种实用且对 (+) - 马约拉诺利德和 (+) - 马约拉诺利德B的合成途径.
- 这些天然产品的绝对配置已经明确确定.
- 这项工作为从可再生资源中合成复杂的自然产品提供了宝贵的见解.
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