Abstract
Using a highly diastereoselective intramolecular acrylate [4+2] cycloaddition as the key step, a short route from 3-furaldehyde to a bicyclic building block for the synthesis of neoclerodane diterpenes was developed. A first attempt featuring a conjugate methylation of a dienyl lactone failed, but a streamlined sequence using an all-encompassing intramolecular Diels-Alder reaction of a sterically congested 1,3-diene was successful. A highly diastereoselective intramolecular acrylate [4+2] cycloaddition of a sterically congested 1,3-diene served as the key step in a short synthesis of a BC building block for neoclerodane diterpenes.
| Original language | English |
|---|---|
| Pages (from-to) | 4083-4088 |
| Number of pages | 6 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2014 |
| Issue number | 19 |
| DOIs | |
| Publication status | Published - 2014 |
Keywords
- Cross-coupling
- Cycloaddition
- Michael addition
- Natural products
- Terpenoids
ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
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Wang, Y., Rogachev, V., Wolter, M., Gruner, M., Jäger, A., & Metz, P. (2014). An approach to the bicyclic C-5-C-17/C-19-C-20 (BC) portion of neoclerodane diterpenes by intramolecular Diels-Alder reaction. European Journal of Organic Chemistry, 2014(19), 4083-4088. https://doi.org/10.1002/ejoc.201402165