A Facile Synthesis of the Angucyclinone Antibiotic (+)-Rubiginone B2  Involving the BF3-Mediated Diels-Alder Reaction of Juglone

Jiro Motoyoshiya; Yusuke Masue; Gento Iwayama; Sachiko Yoshioka; Yoshinori Nishii; Hiromu Aoyama

doi:10.1055/s-2004-829196

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A Facile Synthesis of the Angucyclinone Antibiotic (+)-Rubiginone B₂ Involving the BF₃-Mediated Diels-Alder Reaction of Juglone

Jiro Motoyoshiya*, Yusuke Masue, Gento Iwayama, Sachiko Yoshioka, Yoshinori Nishii, Hiromu Aoyama
Department of Chemistry, Faculty of Textile Science and Technology, Shinshu University, Ueda, Nagano, 386-8567 Japan
Fax: +81(268)215391; e-Mail: jmotoyo@giptc.shinshu-u.ac.jp;

Abstract

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Abstract

A short synthesis of (+)-rubiginone B₂ is reported. The BF₃-mediated Diels-Alder reaction of juglone and (R)-3-methyl-1-vinylcyclohexene followed by aromatization gave the anthraquinone as the desired regioisomer, which was converted into the target antibiotic after a two-step operation.

Key words

angucyclinone antibiotics - asymmetric synthesis - quinines - Diels-Alder reactions - photooxidations

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References

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