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

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.

SUBMITTER: Hutt OE

PROVIDER: S-EPMC3638842 | biostudies-literature | 2013 Apr

REPOSITORIES: biostudies-literature

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

Hutt Oliver E OE Doan Trinh L TL Georg Gunda I GI

Organic letters 20130326 7

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. Thi ...[more]

PMID: 23530630

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