A base-catalyzed Diels–Alder reaction of N-tosyl-3-hydroxy-2-pyridone
✍ Scribed by Hiroaki Okamura; Hiroshi Nagaike; Tetsuo Iwagawa; Munehiro Nakatani
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 114 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
📜 SIMILAR VOLUMES
Asymmetric total synthesis of (+)-epiepoformin was achieved in short steps using the base-catalyzed asymmetric Diels-Alder (DA) reaction of 3-hydroxy-2-pyrone with chiral acrylate. Since the synthesis produced Ogasawara's intermediate, it is also presented as a formal synthesis of (-)-theobroxide.
In the presence of a cinchona alkaloid as a catalyst, the Diels-Alder reaction of 3-hydroxy-2-pyrone with chiral N-acryloyl oxazolidinone afforded a bicyclolactone adduct with high diastereoselectivities (up to 95%de) in almost quantitative yield.