MeAlSEt 促进的多米诺狄克曼环化反应实现了多环多聚异戊烯基酰基间苯三酚的全合成。
MeAlSEt-Promoted Domino Dieckmann Cyclization Enables the Total Synthesis of Polycyclic Polyprenylated Acylphloroglucinols.
机构信息
School of Pharmacy , Shanghai University of Traditional Chinese Medicine , Shanghai 201203 , China.
Key Laboratory of Synthetic Chemistry of Natural Substances , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , Shanghai 200032 , China.
出版信息
Org Lett. 2019 Oct 4;21(19):8075-8079. doi: 10.1021/acs.orglett.9b03078. Epub 2019 Sep 24.
A bioinspired, MeAlSEt-promoted domino Dieckmann cyclization via an 8-membered ring intermediate to construct bicyclo[3.3.1]nonanes was developed, and the divergent syntheses of nine complex polycyclic polyprenylated acylphloroglucinols were achieved. This novel domino cyclization tolerates a series of congested substrates, providing a very efficient way to construct diverse polycyclic structures. The selectivity and the advantages of the domino cyclization were studied. Moreover, the structure-activity relationship study leads to the identification of three simplified potent antitumor agents.
受生物启发，通过一个 8 元环中间体，利用 MeAlSEt 促进多米诺狄克曼环化反应来构建双环[3.3.1]壬烷，实现了九种复杂的多环多聚异戊烯基酰基间苯三酚的发散合成。这种新型的多米诺环化反应能够容忍一系列拥挤的底物，为构建各种多环结构提供了一种非常有效的方法。研究了该多米诺环化反应的选择性和优势。此外，结构-活性关系研究确定了三种简化的强效抗肿瘤剂。
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