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Synthesis of (+)-epiepoformin using the base-catalyzed Diels–Alder reaction of 3-hydroxy-2-pyrone

✍ Scribed by Hideki Shimizu; Hiroaki Okamura; Naomi Yamashita; Tetsuo Iwagawa; Munehiro Nakatani

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
72 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

📜 SIMILAR VOLUMES

Asymmetric base-catalyzed Diels-Alder re
Asymmetric base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone with chiral acrylate derivatives
✍ Hiroaki Okamura; Katsuki Morishige; Tetsuo Iwagawa; Munehiro Nakatani 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 200 KB

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.