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a synthetic strategy based on biogenetic building blocks for the collective and divergent biomimetic synthesis of cleistoperlones a-f, a cinnamoylphloroglucinol collection discovered from cleistocalyx operculatus, has been developed. these syntheses proceeded successfully in only six to seven steps starting from commercially available 1,3,5-benzenetriol and involving oxidative activation of stable biogenetic building blocks 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 the dihydropyrano[3,2-d]xanthene tetracyclic core of cleistoperlones a and b, and a rare inverse-electron-demand hetero-diels-alder cycloaddition for the establishment of benzopyran ring in cleistoperlones d-f. moreover, cleistoperlone a exhibited significant antiviral activity against acyclovir-resistant strains of herpes simplex virus type 1 (hsv-1/blue and hsv-1/153).