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

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

doi:10.1021/ol400385w

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

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

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

36 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 language	English (US)
Pages (from-to)	1602-1605
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	7
DOIs	https://doi.org/10.1021/ol400385w
State	Published - Apr 5 2013

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

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