A synthetic study on antiviral and antioxidative chromene derivative

Chemical & Pharmaceutical Bulletin
Jun MoriHaruo Saito

Abstract

An efficient synthesis of the antiviral and antioxidative chromene (1) was achieved. A small amount of chromene 1 could be derived from plastoquinones 2 and 3, the major constituents of the brown alga, Sargassum micracanthum. By the following synthetic scheme involving its application, many kinds of analogs can be synthesized for evaluation of their biological activity and mechanistic study. The total synthesis of 1, started from geranyl acetate and protected 2-bromo-6-methylhydroquinone, was executed with Sharpless asymmetric dihydroxylation for introduction of the terminal diol system and base-catalyzed sigmatropic rearrangement for construction of the chromene skeleton as the crucial steps. The stereochemistry at C-11' was reconfirmed by this synthesis.

References

Mar 12, 2002·Bioorganic & Medicinal Chemistry·Kenji TerashimaMasatake Niwa
May 16, 2003·Phytotherapy Research : PTR·Jun MoriHaruo Saito

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Citations

Nov 28, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yanyang HeMei Zhang
Mar 24, 2016·Molecular Diversity·Afsaneh ZonouziSeik Weng Ng
Sep 27, 2008·Journal of Natural Products·Misong JungJongheon Shin
Jun 19, 2008·Journal of Combinatorial Chemistry·Xiongjie YuFener Chen

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