Divergent Total Syntheses of Illicium Sesquiterpenes through Late-Stage Skeletal Reorganization.
Journal of the American Chemical Society(2023)
Abstract
We disclose unified, protecting-group-free, bioinspired divergent total syntheses of eight -cedrane and -prezizaane sesquiterpenes and formal syntheses of five anislactone sesquiterpenes. The efficiency of our approach derives from rapid access to the 15-carbon tricyclic carboxylic acid through cationic epoxide-ene cyclization and HAT oxygenation, transformation of this intermediate into three distinct tricyclic precursors via Lewis acid-mediated skeletal reorganizations, subsequent programmed oxidation level enhancement, and a biomimetic oxidation-initiated skeletal rearrangement cascade. Consequently, we created a synthetic correlation map of the three most prevalent sesquiterpene families.
MoreTranslated text
Key words
sesquiterpenes,syntheses,late-stage
AI Read Science
Must-Reading Tree
Example
![](https://originalfileserver.aminer.cn/sys/aminer/pubs/mrt_preview.jpeg)
Generate MRT to find the research sequence of this paper
Chat Paper
Summary is being generated by the instructions you defined