Abstract
A detailed exploration of the synthesis of (-)-morphine based on sequential [3,3]-sigmatropic rearrangements is described. The sequential Claisen/Claisen rearrangements of an allylic vicinal diol resulted in the stereoselective formation of the two contiguous carbon centers, including a sterically encumbered quaternary carbon, in a single operation. The two ethyl esters generated in this reaction were successfully differentiated during a subsequent Friedel-Crafts-type cyclization. The (-)-morphine double bond was introduced at a late stage in our first-generation synthesis, but was formed at an earlier stage in the second-generation synthesis, resulting in a more efficient route to the end product.
| Original language | English |
|---|---|
| Pages (from-to) | 264-269 |
| Number of pages | 6 |
| Journal | Chemistry - A European Journal |
| Volume | 19 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2013 Jan 2 |
Keywords
- allylic compounds
- chirality
- morphine
- sigmatropic rearrangement
- total synthesis
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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Ichiki, M., Tanimoto, H., Miwa, S., Saito, R., Sato, T., & Chida, N. (2013). Synthesis of (-)-morphine: Application of sequential claisen/claisen rearrangement of an allylic vicinal diol. Chemistry - A European Journal, 19(1), 264-269. https://doi.org/10.1002/chem.201203284