Total syntheses of shizukaols A and E

Wu, Jian-Li and Lu, Yin-Suo and Tang, Bencan and Peng, Xiao-Shui (2018) Total syntheses of shizukaols A and E. Nature Communications, 9 . 4040/1-4040/7. ISSN 2041-1723

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Abstract

Shizukaols possess a common heptacyclic framework containing more than ten contiguousstereocenters and potential biological activities. Here we report that the total syntheses ofshizukaols A (1)and E(2), two lindenane-type dimers from the Chloranthaceae family, areachieved via a modified biomimetic Diels–Alder reaction. The common crucial biomimetic diene23and ethylene species (6,17) are obtained through either a highlyZ-selective olefination ofα-siloxy ketone with ynolate anions or an intramolecular Horner–Wadsworth–Emmons olefinationfrom commercially available Wieland–Miescher ketone (7). This synthetic approach here opensup practical avenues for the total syntheses of the intriguing Chloranthaceae family members, aswell as the understanding of their relevant biological action in nature

Item Type: Article
Schools/Departments: University of Nottingham Ningbo China > Faculty of Science and Engineering > Department of Chemical and Environmental Engineering
Identification Number: https://doi.org/10.1038/s41467-018-06245-7
Depositing User: Zhou, Elsie
Date Deposited: 27 Mar 2019 15:41
Last Modified: 27 Mar 2019 16:51
URI: http://eprints.nottingham.ac.uk/id/eprint/56370

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