Synthesis of Skeletally Diverse and Stereochemically Complex Library Templates Derived from Isosteviol and Steviol

详细信息    查看全文

• 作者：Oliver E. Hutt ; Trinh L. Doan ; Gunda I. Georg
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：April 5, 2013
• 年：2013
• 卷：15
• 期：7
• 页码：1602-1605
• 全文大小：266K
• 年卷期：v.15,no.7(April 5, 2013)
• ISSN：1523-7052

文摘

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鈥揨iegler-type cyclization reactions.