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One-pot preparation of 1H-naphtho[2,3-c]pyran-5,10-diones and its application to concise total synthesis of (±)-eleutherin and (±)-isoeleutherin

✍ Scribed by Kazuhiro Kobayashi; Masaharu Uchida; Tomokazu Uneda; Miyuki Tanmatsu; Osamu Morikawa; Hisatoshi Konishi

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
211 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

1H-Naphtho[2,3-c]pyran-5,10-dione derivatives, including a natural product (pentalongin), were generally synthesized in one-pot using a tandem conjugate addition-cyclization sequence between 2-(1-hydroxyalkyl)-1,4naphthoquinones and enamines (or imines). The utility of this method was demonstrated in the synthesis of pyranonaphthoquinone antibiotics, (+)-eleutherin and (+)-isoeleutherin.

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