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A base catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone

✍ Scribed by Hiroaki Okamura; Tetsuo Iwagawa; Munehiro Nakatani

Publisher
Elsevier Science
Year
1995
Tongue
French
Weight
168 KB
Volume
36
Category
Article
ISSN
0040-4039

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πŸ“œ SIMILAR VOLUMES

Synthesis of (+)-epiepoformin using the
Synthesis of (+)-epiepoformin using the base-catalyzed Diels–Alder reaction of 3-hydroxy-2-pyrone
✍ Hideki Shimizu; Hiroaki Okamura; Naomi Yamashita; Tetsuo Iwagawa; Munehiro Nakat πŸ“‚ Article πŸ“… 2001 πŸ› Elsevier Science 🌐 French βš– 72 KB

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.

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Asymmetric base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone with chiral acrylate derivatives
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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.