Mixed Superbase LICKOR as a Key Reagent for the Synthesis of Conjugate Dienes from Citral and Farnesal – A New Route to a Potential Mimic Agent of Juvenile Hormones by Diels–Alder Cycloaddition
✍ Scribed by Paolo Balma Tivola; Annamaria Deagostino; Claudia Fenoglio; Mariella Mella; Cristina Prandi; Paolo Venturello
- Publisher
- John Wiley and Sons
- Year
- 1999
- Tongue
- English
- Weight
- 148 KB
- Volume
- 1999
- Category
- Article
- ISSN
- 1434-193X
No coin nor oath required. For personal study only.
✦ Synopsis
Treatment of the dimethyl acetals of citral (1) and farnesal be subjected to a Diels-Alder reaction, which allows further synthetic elaboration. In particular, in the case of farnesal (2) with the superbase "LICKOR" in THF at low temperatures induces regioselective metallation at the allylic methyl group dimethyl acetal the cycloaddition process leads to a derivative that can be transformed into a potential mimic at C(3). The metal-hydrogen exchange promotes immediate 1,4-elimination, yielding an (E)-configured conjugate agent of Juvenile hormones. alkyloxy-functionalized diene.