期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 30, 页码 16655-16660出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202105395
关键词
asymmetric synthesis; lignans; natural products; photoinduced cycloaddition; total synthesis
资金
- National Natural Science Foundation of China [21971068, 21772044]
- Program of Shanghai Academic/Technology Research Leaders [18XD1401500]
- Program of Shanghai Science and Technology Committee [18JC1411303]
- Shuguang Program [19SG21]
- Fundamental Research Funds for the Central Universities
This study developed a new synthetic method for constructing aryltetralin lactone lignans and successfully synthesized several natural lignans using this methodology. The synthesized aglacins and small-molecule library created new opportunities for SAR studies of the podophyllotoxin family of natural products.
An asymmetric photoenolization/Diels-Alder (PEDA) reaction between electron-rich 2-methylbenzaldehydes and unsaturated gamma-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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