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One‐Pot Synthesis of 2‐Arylthio‐2‐cyclohexenone Derivatives by the Diels–Alder Reaction of 4‐Arylthio‐3‐hydroxy‐2‐pyrones
✍ Scribed by Komiyama, Takuzo; Takaguchi, Yutaka; Tsuboi, Sadao
- Book ID
- 126556428
- Publisher
- Taylor and Francis Group
- Year
- 2007
- Tongue
- English
- Weight
- 82 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0039-7911
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📜 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.