Biomimetic Synthesis of an Antiviral Cinnamoylphloroglucinol Collection from Cleistocalyx operculatus: A Synthesis Strategy Based on Biogenetic Building Blocks
Biomimetic Synthesis of an Antiviral Cinnamoylphloroglucinol Collection from Cleistocalyx operculatus: A Synthesis Strategy Based on Biogenetic Building Blocks
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DOI：
10.1002/anie.202312568
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发表时间：
2023
期刊：
影响因子：
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通讯作者：
Ye Wen-Cai
中科院分区：
文献类型：
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作者：
Wang Jie;Song Jian-Guo;Zhong Dong-Lin;Duan Zhi-Zhang;Peng Zi-Jian;Tang Wei;Song Qiao-Yun;Huang Xiao-Jun;Hu Li-Jun;Wang Ying;Ye Wen-Cai
A synthesis strategy based on biogenetic building blocks for the collective and divergent biomimetic syntheses of cleistoperlones A–F (1–6), a cinnamoylphloroglucinol collection discovered from Cleistocalyx operculatus, has been developed. These syntheses were proceeded successfully in only six to seven steps starting from the commercially available 1,3,5‐benzenetriol involving oxidative activation of stable biogenetic building blocks into activated forms as a crucial step. Key features of the syntheses include a unique Michael addition/ketalization/1,6‐addition/enol‐keto tautomerism cascade reaction for the construction of dihydropyrano[3,2‐d]xanthene tetracyclic core of 1 and 2, and a rare inverse electron demand hetero‐Diels–Alder cycloaddition for the establishment of benzopyran ring in 4–6. Moreover, compound 1 exhibited significant antiviral activity against acyclovir‐resistant strains of herpes simplex virus type 1 (HSV‐1/Blue and HSV‐1/153).
