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

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

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1602-1605
Number of pages4
JournalOrganic Letters
Volume15
Issue number7
DOIs
StatePublished - Apr 5 2013

Fingerprint Dive into the research topics of 'Synthesis of skeletally diverse and stereochemically complex library templates derived from isosteviol and steviol'. Together they form a unique fingerprint.

Cite this