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 |
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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