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Biomimetic asymmetric total syntheses of spirooliganones A and B

Organic Letters, ISSN: 1523-7052, Vol: 16, Issue: 14, Page: 3740-3743
2014
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Article Description

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. © 2014 American Chemical Society.

Bibliographic Details

Song, Liyan; Yao, Hongliang; Tong, Rongbiao

American Chemical Society (ACS)

Biochemistry, Genetics and Molecular Biology; Chemistry

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