Asymmetric Total Synthesis of Aglacins A, B, and E
Mengmeng Xu1, Min Hou1, Haibing He2
1Shanghai Key Laboratory of Green Chemistry and Chemical, Processes, School of Chemistry and Molecular Engineering, East China Normal University, China.
Abstract:
An asymmetric photoenolization/Diels-Alder (PEDA) reaction between electron-rich 2-methylbenzaldehydes and unsaturated γ-lactones was developed to directly construct the basic tricyclic core of aryltetralin lactone lignans. This methodology enabled the first asymmetric total synthesis of aglacins A, B, and E and revision of the absolute configuration of these natural lignans. The strategy was also used to prepare the naturally occurring aryldihydronaphthalene-type lignans (-)-7,8-dihydroisojusticidin B and (+)-linoxepin in four and six steps, as well as 27 natural-product-like molecules containing a C8' quaternary center. We believe that the synthetic aglacins and small-molecule library provide new opportunities to carry out the SAR studies of the podophyllotoxin family of natural products.
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