Biomimetic asymmetric total syntheses of spirooliganones A and B
Liyan Song1, Hongliang Yao, Rongbiao Tong
1Department of Chemistry, The Hong Kong University of Science and Technology , Clear Water Bay, Kowloon, Hong Kong, China.
Abstract:
Biomimetic total syntheses of potent antiviral spirooliganones A and B were achieved with 3% and 2% yield, respectively, in 12 steps from commercially available materials. The synthetic strategy was inspired primarily by the biogenetic hypothesis and was enabled by two independent cascade events: (i) an unprecedented reaction involving aromatic Claisen rearrangement/o-quinone methide formation/hetero-Diels-Alder cycloaddition to construct the tetracyclic framework and (ii) phenol oxidative dearomatization/spirocyclization to build the spiro-fused cyclohexadienone/tetrahydrofuran moiety.
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