Synthesis of skeletally diverse and stereochemically complex library templates derived from isosteviol and steviol.

Synthesis of skeletally diverse and stereochemically complex library templates derived from isosteviol and steviol.
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DOI:
10.1021/ol400385w
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发表时间:
2013-04-05
期刊:
影响因子:
5.2
通讯作者:
Georg, Gunda I.
Georg, Gunda I.
中科院分区:
化学1区
文献类型:
--
作者:
Hutt, Oliver E.;Doan, Trinh L.;Georg, Gunda I.

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We have applied a diversity-oriented approach for the synthesis of skeletally diverse and stereochemically complex templates for small-molecule library production by performing Beckmann rearrangement and Beckmann fragmentation reactions on the bicyclo[3.2.1]octane rings of steviol and isosteviol, aglycones derived from the diterpene natural product stevioside. The optimization of these two reaction pathways is presented along with the successful application of a photo-Beckmann rearrangement. This work also led to the discovery of cyano-Prins-type and Thorpe-Ziegler-type cyclization reactions.
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