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不对称的塞法洛坦类型的迪特尔化物A-D的总合成

Zhineng Qing¹, Peng Mao¹, Tie Wang¹

¹The State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Nano-Micro Materials Research, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen 518055, China.

Journal of the American Chemical Society

|June 2, 2022

概括

研究人员成功合成了四种A-D类,它们是具有独特四环核的新型二类. 这项研究展示了Diels-Alder和催化循环添加等关键反应,用于构建复杂的自然产品.

科学领域:

有机化学
自然产品合成
医学化学

背景情况:

塞法洛坦类型的二烯酸是复杂的天然产品.
塞法诺利德A-D具有独特的6/6/6/5四环结构,其中包含一个桥接的delta-lactone.
这些化合物的复杂结构带来了重大合成挑战.

研究的目的:

为了实现A-D的不对称和分离的总合成.
开发和展示用于构建复杂四环核的新型合成方法.
为进一步的生物评估提供这些天然产品.

主要方法:

采用基质控制的二分体选择性分子间迪尔斯-阿尔德反应来构建 cis-fused 6-6 环系统.
使用催化形式的双分子 [2+2+2] 循环添加,涉及一连串的碳金属化,用于组装四环骨架.
进行了乳化和晚期氧化功能化步骤以完成合成.

主要成果:

从已知的酒精前体中成功完成了CEPHANOLIDE A-D的总合成.
合成途径有效地确定了新的6/6/6/5四环核和桥接的三角乳.
主要的立体中心通过二分立体选择和催化反应进行控制.

结论:

这项研究证明了A-D全合成的可行和有效策略.
使用的合成方法,包括迪尔斯-阿尔德和催化循环添加,是构建复杂多环系统的强大工具.
这项工作扩大了化物天然产品的可获得性,并为探索其化学空间提供了基础.

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