Biomimetic Synthesis of an Antiviral Cinnamoylphloroglucinol Collection from Cleistocalyx operculatus: A Synthesis Strategy Based on Biogenetic Building Blocks

Angew Chem Int Ed Engl. 2023 Oct 17:e202312568. doi: 10.1002/anie.202312568. Online ahead of print.ABSTRACTA 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).PMID:37848394 | DOI:10.1002/anie.202312568
Source: Herpes - Category: Infectious Diseases Authors: Source Type: research