A facile synthesis of asterriquinone D
β Scribed by Yasuhiro Tanoue; Takashi Motoi; Yutaka Masuda; Norihisa Kai; Kazunori Sakata; Mamoru Hashimoto; Takeshi Nagai
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2008
- Tongue
- English
- Weight
- 229 KB
- Volume
- 45
- Category
- Article
- ISSN
- 0022-152X
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β¦ Synopsis
Abstract
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Asterriquinone D was easily synthesized in three steps from 2,5βdichloroβ1,4βbenzoquinone. The reaction of benzoquinone with indole in the presence of Pd(OAc)~2~, followed by oxidation with cerium (IV) ammonium nitrate (CAN) produced 3,6βdichloroβ2,5βbis (3βindolyl)β1,4βbenzoquinone. The methoxylation of the dichloride with NaOH in CH~3~OH afforded asterriquinone D.
π SIMILAR VOLUMES
This communication describes the first total synthesis of asterriquinone B 1, a representative member of a group of anti-tumor metabolites of Aspergillus terreus. The synthesis described herein is potentially applicable to other members of the asterriquinone family.
During the preparation of simple mannopyranosides using the Koenigs-Knorr type reaction, we observed that a significant amount of disaccharide glycoside was produced when the alcohol was used in amounts less than equivalent of 2,3,4,6-tetra-O-acetyl-c~-D-mannopyranosyl bromide ("acetobromomannose").