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Literature DB >> 23530630

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

Oliver E Hutt¹, Trinh L Doan, Gunda I Georg.

Abstract

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.

Entities: Chemical Disease Gene Mutation

Mesh：

Substances：

Year: 2013 PMID： 23530630 PMCID： PMC3638842 DOI： 10.1021/ol400385w

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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